Ichikawa Y, Ichikawa R, Kuzuhara H
Carbohydr Res. 1985 Sep 1;141(2):273-82. doi: 10.1016/s0008-6215(00)90458-0.
O-(2-Deoxy-2-sulfamido-6-O-sulfo-alpha-D-glucopyranosyl)-(1----4)- O-(beta-D- glucopyranosyluronic acid)-(1----4)-1,6-anhydro-2-deoxy-2-sulfamido-6-O-sulfo-beta-D-gl ucopyranose pentasodium salt (14) was synthesized as a heparin-related oligosaccharide. The glycosyl acceptor (derived from cellobiose) and a glycosyl donor, 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-alpha-D-glucopyranosyl bromide, were coupled in the presence of mercuric bromide and molecular sieves 4A to afford a 69% yield of fully protected trisaccharide, namely, O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-alpha-D-glucopyranosyl)-(1 ----4)- O-(methyl 2,3-di-O-benzyl-beta-D-glucopyranosyluronate)-(1----4)-3-O-acetyl- 1,6-anhydro-2 - azido-2-deoxy-beta-D-glucopyranose (10), which was converted into the partially sulfated trisaccharide 14. Compound 10 also underwent acetolysis to afford the glycosyl acetate, for further elongation of the glycosyl chain.
O-(2-脱氧-2-氨磺酰基-6-O-磺基-α-D-吡喃葡萄糖基)-(1→4)-O-(β-D-吡喃葡萄糖醛酸)-(1→4)-1,6-脱水-2-脱氧-2-氨磺酰基-6-O-磺基-β-D-吡喃葡萄糖五钠盐(14)被合成为一种肝素相关寡糖。糖基受体(源自纤维二糖)和糖基供体6-O-乙酰基-2-叠氮基-3,4-二-O-苄基-2-脱氧-α-D-吡喃葡萄糖基溴在溴化汞和4A分子筛存在下偶联，以69%的产率得到完全保护的三糖，即O-(6-O-乙酰基-2-叠氮基-3,4-二-O-苄基-2-脱氧-α-D-吡喃葡萄糖基)-(1→4)-O-(甲基2,3-二-O-苄基-β-D-吡喃葡萄糖醛酸酯)-(1→4)-3-O-乙酰基-1,6-脱水-2-叠氮基-2-脱氧-β-D-吡喃葡萄糖(10)，其被转化为部分硫酸化的三糖14。化合物10也进行乙酰解以得到糖基乙酸酯，用于糖基链的进一步延长。
