char = R;code = 82 char = e;code = 101 char = d;code = 100 char = u;code = 117 char = c;code = 99 char = t;code = 116 char = i;code = 105 char = v;code = 118 char = e;code = 101 char = ;code = 32 char = f;code = 102 char = r;code = 114 char = a;code = 97 char = g;code = 103 char = m;code = 109 char = e;code = 101 char = n;code = 110 char = t;code = 116 char = a;code = 97 char = t;code = 116 char = i;code = 105 char = o;code = 111 char = n;code = 110 char = ;code = 32 char = o;code = 111 char = f;code = 102 char = ;code = 32 char = c;code = 99 char = a;code = 97 char = r;code = 114 char = b;code = 98 char = o;code = 111 char = h;code = 104 char = y;code = 121 char = d;code = 100 char = r;code = 114 char = a;code = 97 char = t;code = 116 char = e;code = 101 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = o;code = 111 char = m;code = 109 char = e;code = 101 char = r;code = 114 char = i;code = 105 char = c;code = 99 char = ;code = 32 char = a;code = 97 char = l;code = 108 char = k;code = 107 char = o;code = 111 char = x;code = 120 char = y;code = 121 char = ;code = 32 char = r;code = 114 char = a;code = 97 char = d;code = 100 char = i;code = 105 char = c;code = 99 char = a;code = 97 char = l;code = 108 char = s;code = 115 char = .;code = 46 char = ;code = 32 char = S;code = 83 char = y;code = 121 char = n;code = 110 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = s;code = 115 char = i;code = 105 char = s;code = 115 char = ;code = 32 char = o;code = 111 char = f;code = 102 char = ;code = 32 char = a;code = 97 char = l;code = 108 char = d;code = 100 char = i;code = 105 char = t;code = 116 char = o;code = 111 char = l;code = 108 char = s;code = 115 char = ;code = 32 char = w;code = 119 char = i;code = 105 char = t;code = 116 char = h;code = 104 char = ;code = 32 char = p;code = 112 char = o;code = 111 char = t;code = 116 char = e;code = 101 char = n;code = 110 char = t;code = 116 char = i;code = 105 char = a;code = 97 char = l;code = 108 char = ;code = 32 char = u;code = 117 char = t;code = 116 char = i;code = 105 char = l;code = 108 char = i;code = 105 char = t;code = 116 char = y;code = 121 char = ;code = 32 char = a;code = 97 char = s;code = 115 char = ;code = 32 char = c;code = 99 char = h;code = 104 char = i;code = 105 char = r;code = 114 char = a;code = 97 char = l;code = 108 char = ;code = 32 char = s;code = 115 char = y;code = 121 char = n;code = 110 char = t;code = 116 char = h;code = 104 char = o;code = 111 char = n;code = 110 char = s;code = 115 char = .;code = 46 result sql = Reductive fragmentation of carbohydrate anomeric alkoxy radicals. Synthesis of alditols with potential utility as chiral synthons.
Reductive fragmentation of carbohydrate anomeric alkoxy radicals. Synthesis of alditols with potential utility as chiral synthons.char = A;code = 65 char = ;code = 32 char = s;code = 115 char = e;code = 101 char = r;code = 114 char = i;code = 105 char = e;code = 101 char = s;code = 115 char = ;code = 32 char = o;code = 111 char = f;code = 102 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = o;code = 111 char = m;code = 109 char = e;code = 101 char = r;code = 114 char = i;code = 105 char = c;code = 99 char = ;code = 32 char = n;code = 110 char = i;code = 105 char = t;code = 116 char = r;code = 114 char = a;code = 97 char = t;code = 116 char = e;code = 101 char = ;code = 32 char = e;code = 101 char = s;code = 115 char = t;code = 116 char = e;code = 101 char = r;code = 114 char = s;code = 115 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = N;code = 78 char = -;code = 45 char = p;code = 112 char = h;code = 104 char = t;code = 116 char = h;code = 104 char = a;code = 97 char = l;code = 108 char = i;code = 105 char = m;code = 109 char = i;code = 105 char = d;code = 100 char = o;code = 111 char = ;code = 32 char = g;code = 103 char = l;code = 108 char = y;code = 121 char = c;code = 99 char = o;code = 111 char = s;code = 115 char = i;code = 105 char = d;code = 100 char = e;code = 101 char = s;code = 115 char = ;code = 32 char = o;code = 111 char = f;code = 102 char = ;code = 32 char = c;code = 99 char = a;code = 97 char = r;code = 114 char = b;code = 98 char = o;code = 111 char = h;code = 104 char = y;code = 121 char = d;code = 100 char = r;code = 114 char = a;code = 97 char = t;code = 116 char = e;code = 101 char = s;code = 115 char = ;code = 32 char = i;code = 105 char = n;code = 110 char = ;code = 32 char = f;code = 102 char = u;code = 117 char = r;code = 114 char = a;code = 97 char = n;code = 110 char = o;code = 111 char = s;code = 115 char = e;code = 101 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = p;code = 112 char = y;code = 121 char = r;code = 114 char = a;code = 97 char = n;code = 110 char = o;code = 111 char = s;code = 115 char = e;code = 101 char = ;code = 32 char = f;code = 102 char = o;code = 111 char = r;code = 114 char = m;code = 109 char = s;code = 115 char = ;code = 32 char = h;code = 104 char = a;code = 97 char = v;code = 118 char = e;code = 101 char = ;code = 32 char = b;code = 98 char = e;code = 101 char = e;code = 101 char = n;code = 110 char = ;code = 32 char = s;code = 115 char = y;code = 121 char = n;code = 110 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = s;code = 115 char = i;code = 105 char = z;code = 122 char = e;code = 101 char = d;code = 100 char = ;code = 32 char = i;code = 105 char = n;code = 110 char = ;code = 32 char = o;code = 111 char = r;code = 114 char = d;code = 100 char = e;code = 101 char = r;code = 114 char = ;code = 32 char = t;code = 116 char = o;code = 111 char = ;code = 32 char = g;code = 103 char = e;code = 101 char = n;code = 110 char = e;code = 101 char = r;code = 114 char = a;code = 97 char = t;code = 116 char = e;code = 101 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = ;code = 32 char = c;code = 99 char = o;code = 111 char = r;code = 114 char = r;code = 114 char = e;code = 101 char = s;code = 115 char = p;code = 112 char = o;code = 111 char = n;code = 110 char = d;code = 100 char = i;code = 105 char = n;code = 110 char = g;code = 103 char = ;code = 32 char = a;code = 97 char = l;code = 108 char = k;code = 107 char = o;code = 111 char = x;code = 120 char = y;code = 121 char = ;code = 32 char = r;code = 114 char = a;code = 97 char = d;code = 100 char = i;code = 105 char = c;code = 99 char = a;code = 97 char = l;code = 108 char = s;code = 115 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = s;code = 115 char = t;code = 116 char = u;code = 117 char = d;code = 100 char = y;code = 121 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = ;code = 32 char = C;code = 67 char = 1;code = 49 char = -;code = 45 char = C;code = 67 char = 2;code = 50 char = ;code = 32 char = f;code = 102 char = r;code = 114 char = a;code = 97 char = g;code = 103 char = m;code = 109 char = e;code = 101 char = n;code = 110 char = t;code = 116 char = a;code = 97 char = t;code = 116 char = i;code = 105 char = o;code = 111 char = n;code = 110 char = ;code = 32 char = r;code = 114 char = e;code = 101 char = a;code = 97 char = c;code = 99 char = t;code = 116 char = i;code = 105 char = o;code = 111 char = n;code = 110 char = ;code = 32 char = u;code = 117 char = n;code = 110 char = d;code = 100 char = e;code = 101 char = r;code = 114 char = ;code = 32 char = r;code = 114 char = e;code = 101 char = d;code = 100 char = u;code = 117 char = c;code = 99 char = t;code = 116 char = i;code = 105 char = v;code = 118 char = e;code = 101 char = ;code = 32 char = c;code = 99 char = o;code = 111 char = n;code = 110 char = d;code = 100 char = i;code = 105 char = t;code = 116 char = i;code = 105 char = o;code = 111 char = n;code = 110 char = s;code = 115 char = .;code = 46 char = ;code = 32 char = T;code = 84 char = h;code = 104 char = i;code = 105 char = s;code = 115 char = ;code = 32 char = r;code = 114 char = e;code = 101 char = a;code = 97 char = c;code = 99 char = t;code = 116 char = i;code = 105 char = o;code = 111 char = n;code = 110 char = ;code = 32 char = c;code = 99 char = o;code = 111 char = n;code = 110 char = s;code = 115 char = t;code = 116 char = i;code = 105 char = t;code = 116 char = u;code = 117 char = t;code = 116 char = e;code = 101 char = s;code = 115 char = ;code = 32 char = a;code = 97 char = ;code = 32 char = t;code = 116 char = w;code = 119 char = o;code = 111 char = -;code = 45 char = s;code = 115 char = t;code = 116 char = e;code = 101 char = p;code = 112 char = ;code = 32 char = m;code = 109 char = e;code = 101 char = t;code = 116 char = h;code = 104 char = o;code = 111 char = d;code = 100 char = ;code = 32 char = f;code = 102 char = o;code = 111 char = r;code = 114 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = ;code = 32 char = t;code = 116 char = r;code = 114 char = a;code = 97 char = n;code = 110 char = s;code = 115 char = f;code = 102 char = o;code = 111 char = r;code = 114 char = m;code = 109 char = a;code = 97 char = t;code = 116 char = i;code = 105 char = o;code = 111 char = n;code = 110 char = ;code = 32 char = o;code = 111 char = f;code = 102 char = ;code = 32 char = c;code = 99 char = a;code = 97 char = r;code = 114 char = b;code = 98 char = o;code = 111 char = h;code = 104 char = y;code = 121 char = d;code = 100 char = r;code = 114 char = a;code = 97 char = t;code = 116 char = e;code = 101 char = s;code = 115 char = ;code = 32 char = i;code = 105 char = n;code = 110 char = t;code = 116 char = o;code = 111 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = ;code = 32 char = c;code = 99 char = o;code = 111 char = r;code = 114 char = r;code = 114 char = e;code = 101 char = s;code = 115 char = p;code = 112 char = o;code = 111 char = n;code = 110 char = d;code = 100 char = i;code = 105 char = n;code = 110 char = g;code = 103 char = ;code = 32 char = a;code = 97 char = l;code = 108 char = d;code = 100 char = i;code = 105 char = t;code = 116 char = o;code = 111 char = l;code = 108 char = s;code = 115 char = ;code = 32 char = w;code = 119 char = i;code = 105 char = t;code = 116 char = h;code = 104 char = ;code = 32 char = o;code = 111 char = n;code = 110 char = e;code = 101 char = ;code = 32 char = l;code = 108 char = e;code = 101 char = s;code = 115 char = s;code = 115 char = ;code = 32 char = c;code = 99 char = a;code = 97 char = r;code = 114 char = b;code = 98 char = o;code = 111 char = n;code = 110 char = .;code = 46 char = ;code = 32 char = U;code = 85 char = s;code = 115 char = i;code = 105 char = n;code = 110 char = g;code = 103 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = i;code = 105 char = s;code = 115 char = ;code = 32 char = m;code = 109 char = e;code = 101 char = t;code = 116 char = h;code = 104 char = o;code = 111 char = d;code = 100 char = o;code = 111 char = l;code = 108 char = o;code = 111 char = g;code = 103 char = y;code = 121 char = ,;code = 44 char = ;code = 32 char = i;code = 105 char = n;code = 110 char = t;code = 116 char = e;code = 101 char = r;code = 114 char = e;code = 101 char = s;code = 115 char = t;code = 116 char = i;code = 105 char = n;code = 110 char = g;code = 103 char = ;code = 32 char = f;code = 102 char = o;code = 111 char = u;code = 117 char = r;code = 114 char = -;code = 45 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = f;code = 102 char = i;code = 105 char = v;code = 118 char = e;code = 101 char = -;code = 45 char = c;code = 99 char = a;code = 97 char = r;code = 114 char = b;code = 98 char = o;code = 111 char = n;code = 110 char = ;code = 32 char = b;code = 98 char = u;code = 117 char = i;code = 105 char = l;code = 108 char = d;code = 100 char = i;code = 105 char = n;code = 110 char = g;code = 103 char = ;code = 32 char = b;code = 98 char = l;code = 108 char = o;code = 111 char = c;code = 99 char = k;code = 107 char = s;code = 115 char = ;code = 32 char = f;code = 102 char = o;code = 111 char = r;code = 114 char = ;code = 32 char = n;code = 110 char = a;code = 97 char = t;code = 116 char = u;code = 117 char = r;code = 114 char = a;code = 97 char = l;code = 108 char = ;code = 32 char = p;code = 112 char = r;code = 114 char = o;code = 111 char = d;code = 100 char = u;code = 117 char = c;code = 99 char = t;code = 116 char = s;code = 115 char = ;code = 32 char = s;code = 115 char = y;code = 121 char = n;code = 110 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = s;code = 115 char = i;code = 105 char = s;code = 115 char = ;code = 32 char = p;code = 112 char = o;code = 111 char = s;code = 115 char = s;code = 115 char = e;code = 101 char = s;code = 115 char = s;code = 115 char = i;code = 105 char = n;code = 110 char = g;code = 103 char = ;code = 32 char = D;code = 68 char = -;code = 45 char = e;code = 101 char = r;code = 114 char = y;code = 121 char = t;code = 116 char = h;code = 104 char = r;code = 114 char = i;code = 105 char = t;code = 116 char = o;code = 111 char = l;code = 108 char = ,;code = 44 char = ;code = 32 char = D;code = 68 char = -;code = 45 char = t;code = 116 char = h;code = 104 char = r;code = 114 char = e;code = 101 char = i;code = 105 char = t;code = 116 char = o;code = 111 char = l;code = 108 char = ,;code = 44 char = ;code = 32 char = D;code = 68 char = -;code = 45 char = x;code = 120 char = y;code = 121 char = l;code = 108 char = i;code = 105 char = t;code = 116 char = o;code = 111 char = l;code = 108 char = ,;code = 44 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = D;code = 68 char = -;code = 45 char = a;code = 97 char = r;code = 114 char = a;code = 97 char = b;code = 98 char = i;code = 105 char = n;code = 110 char = i;code = 105 char = t;code = 116 char = o;code = 111 char = l;code = 108 char = ;code = 32 char = s;code = 115 char = t;code = 116 char = e;code = 101 char = r;code = 114 char = e;code = 101 char = o;code = 111 char = c;code = 99 char = h;code = 104 char = e;code = 101 char = m;code = 109 char = i;code = 105 char = s;code = 115 char = t;code = 116 char = r;code = 114 char = y;code = 121 char = ;code = 32 char = h;code = 104 char = a;code = 97 char = v;code = 118 char = e;code = 101 char = ;code = 32 char = b;code = 98 char = e;code = 101 char = e;code = 101 char = n;code = 110 char = ;code = 32 char = p;code = 112 char = r;code = 114 char = e;code = 101 char = p;code = 112 char = a;code = 97 char = r;code = 114 char = e;code = 101 char = d;code = 100 char = .;code = 46 char = ;code = 32 char = T;code = 84 char = h;code = 104 char = e;code = 101 char = ;code = 32 char = s;code = 115 char = y;code = 121 char = n;code = 110 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = s;code = 115 char = i;code = 105 char = s;code = 115 char = ;code = 32 char = o;code = 111 char = f;code = 102 char = ;code = 32 char = 1;code = 49 char = ,;code = 44 char = 2;code = 50 char = -;code = 45 char = O;code = 79 char = -;code = 45 char = i;code = 105 char = s;code = 115 char = o;code = 111 char = p;code = 112 char = r;code = 114 char = o;code = 111 char = p;code = 112 char = y;code = 121 char = l;code = 108 char = i;code = 105 char = d;code = 100 char = e;code = 101 char = n;code = 110 char = e;code = 101 char = -;code = 45 char = b;code = 98 char = e;code = 101 char = t;code = 116 char = a;code = 97 char = -;code = 45 char = L;code = 76 char = -;code = 45 char = t;code = 116 char = h;code = 104 char = r;code = 114 char = e;code = 101 char = o;code = 111 char = s;code = 115 char = e;code = 101 char = ;code = 32 char = (;code = 40 char = 4;code = 52 char = 0;code = 48 char = );code = 41 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = 1;code = 49 char = -;code = 45 char = a;code = 97 char = c;code = 99 char = e;code = 101 char = t;code = 116 char = a;code = 97 char = m;code = 109 char = i;code = 105 char = d;code = 100 char = o;code = 111 char = -;code = 45 char = 2;code = 50 char = ,;code = 44 char = 4;code = 52 char = ,;code = 44 char = 5;code = 53 char = -;code = 45 char = t;code = 116 char = r;code = 114 char = i;code = 105 char = -;code = 45 char = O;code = 79 char = -;code = 45 char = a;code = 97 char = c;code = 99 char = e;code = 101 char = t;code = 116 char = y;code = 121 char = l;code = 108 char = -;code = 45 char = D;code = 68 char = -;code = 45 char = a;code = 97 char = r;code = 114 char = a;code = 97 char = b;code = 98 char = i;code = 105 char = n;code = 110 char = i;code = 105 char = t;code = 116 char = o;code = 111 char = l;code = 108 char = ;code = 32 char = (;code = 40 char = 5;code = 53 char = 0;code = 48 char = );code = 41 char = ;code = 32 char = h;code = 104 char = a;code = 97 char = v;code = 118 char = e;code = 101 char = ;code = 32 char = a;code = 97 char = l;code = 108 char = s;code = 115 char = o;code = 111 char = ;code = 32 char = b;code = 98 char = e;code = 101 char = e;code = 101 char = n;code = 110 char = ;code = 32 char = a;code = 97 char = c;code = 99 char = h;code = 104 char = i;code = 105 char = e;code = 101 char = v;code = 118 char = e;code = 101 char = d;code = 100 char = ;code = 32 char = f;code = 102 char = r;code = 114 char = o;code = 111 char = m;code = 109 char = ;code = 32 char = 1;code = 49 char = ,;code = 44 char = 2;code = 50 char = :;code = 58 char = 5;code = 53 char = ,;code = 44 char = 6;code = 54 char = -;code = 45 char = d;code = 100 char = i;code = 105 char = -;code = 45 char = O;code = 79 char = -;code = 45 char = i;code = 105 char = s;code = 115 char = o;code = 111 char = p;code = 112 char = r;code = 114 char = o;code = 111 char = p;code = 112 char = y;code = 121 char = l;code = 108 char = i;code = 105 char = d;code = 100 char = e;code = 101 char = n;code = 110 char = e;code = 101 char = -;code = 45 char = b;code = 98 char = e;code = 101 char = t;code = 116 char = a;code = 97 char = -;code = 45 char = D;code = 68 char = -;code = 45 char = g;code = 103 char = l;code = 108 char = u;code = 117 char = c;code = 99 char = o;code = 111 char = f;code = 102 char = u;code = 117 char = r;code = 114 char = a;code = 97 char = n;code = 110 char = o;code = 111 char = s;code = 115 char = e;code = 101 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = 2;code = 50 char = -;code = 45 char = a;code = 97 char = c;code = 99 char = e;code = 101 char = t;code = 116 char = a;code = 97 char = m;code = 109 char = i;code = 105 char = d;code = 100 char = o;code = 111 char = -;code = 45 char = 3;code = 51 char = ,;code = 44 char = 4;code = 52 char = ,;code = 44 char = 6;code = 54 char = -;code = 45 char = t;code = 116 char = r;code = 114 char = i;code = 105 char = -;code = 45 char = O;code = 79 char = -;code = 45 char = a;code = 97 char = c;code = 99 char = e;code = 101 char = t;code = 116 char = y;code = 121 char = l;code = 108 char = -;code = 45 char = 2;code = 50 char = -;code = 45 char = d;code = 100 char = e;code = 101 char = o;code = 111 char = x;code = 120 char = y;code = 121 char = -;code = 45 char = D;code = 68 char = -;code = 45 char = g;code = 103 char = l;code = 108 char = u;code = 117 char = c;code = 99 char = o;code = 111 char = p;code = 112 char = y;code = 121 char = r;code = 114 char = a;code = 97 char = n;code = 110 char = o;code = 111 char = s;code = 115 char = e;code = 101 char = ,;code = 44 char = ;code = 32 char = r;code = 114 char = e;code = 101 char = s;code = 115 char = p;code = 112 char = e;code = 101 char = c;code = 99 char = t;code = 116 char = i;code = 105 char = v;code = 118 char = e;code = 101 char = l;code = 108 char = y;code = 121 char = .;code = 46 char = <;code = 60 char = b;code = 98 char = r;code = 114 char = /;code = 47 char = >;code = 62 result sql = A series of anomeric nitrate esters and N-phthalimido glycosides of carbohydrates in furanose and pyranose forms have been synthesized in order to generate the corresponding alkoxy radicals and study the C1-C2 fragmentation reaction under reductive conditions. This reaction constitutes a two-step method for the transformation of carbohydrates into the corresponding alditols with one less carbon. Using this methodology, interesting four- and five-carbon building blocks for natural products synthesis possessing D-erythritol, D-threitol, D-xylitol, and D-arabinitol stereochemistry have been prepared. The synthesis of 1,2-O-isopropylidene-beta-L-threose (40) and 1-acetamido-2,4,5-tri-O-acetyl-D-arabinitol (50) have also been achieved from 1,2:5,6-di-O-isopropylidene-beta-D-glucofuranose and 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranose, respectively.
Publication: J. Org. Chem. 2001 Oct 19 ;66(21)::6967-76.
Publication Date: 2001 Oct 19
Study Author(s): Francisco, C G;León, E I;Martín, A;Moreno, P;Rodríguez, M S;Suárez, E;
Institution: Instituto de Productos Naturales y Agrobiología del CSIC, Carretera de La Esperanza 3, 38206-La Laguna, Tenerife, Spain.
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A series of anomeric nitrate esters and N-phthalimido glycosides of carbohydrates in furanose and pyranose forms have been synthesized in order to generate the corresponding alkoxy radicals and study the C1-C2 fragmentation reaction under reductive conditions. This reaction constitutes a two-step method for the transformation of carbohydrates into the corresponding alditols with one less carbon. Using this methodology, interesting four- and five-carbon building blocks for natural products synthesis possessing D-erythritol, D-threitol, D-xylitol, and D-arabinitol stereochemistry have been prepared. The synthesis of 1,2-O-isopropylidene-beta-L-threose (40) and 1-acetamido-2,4,5-tri-O-acetyl-D-arabinitol (50) have also been achieved from 1,2:5,6-di-O-isopropylidene-beta-D-glucofuranose and 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranose, respectively.
PMID: 11597215