与绒毛膜癌患者人绒毛膜促性腺激素双天线聚糖链相关的七糖半抗原的合成。一种汇聚法。
Synthesis of a heptasaccharide hapten related to a biantennary glycan chain of human chorionic gonadotropin of a choriocarcinoma patient. A convergent approach.
作者信息
Sadozai K K, Nukada T, Ito Y, Nakahara Y, Ogawa T, Kobata A
出版信息
Carbohydr Res. 1986 Dec 1;157:101-23. doi: 10.1016/0008-6215(86)85063-7.
Synthesis of the heptasaccharide hapten 8-methoxycarbonyloctyl O-beta-D-galactopyranosyl-(1----4)-O-(2-acetamido-2-deoxy-beta-D- glucopyranosyl)-(1----2)-O-[beta-D-galactopyranosyl-(1----4)-O-(2-acetam ido-2- deoxy-beta-D-glucopyranosyl)-(1----4)]-O-alpha-D-mannopyranosyl-(1----3) -O- [alpha-D-mannopyranosyl-(1----6)]-beta-D-mannopyranoside is described, by use of the known, protected glycosyl acceptor 8-ethoxy-carbonyloctyl O-(2,3,4,6-tetra-O-benzyl-alpha-D-mannopyranosyl)-(1----6)-2,4-di-O-benz yl-beta - D-mannopyranoside, and the key glycopentaosyl donors O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-(1----4)-O-(2-acetami do-3,6- di-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-(1----2)-O-[(2,3,4,6-tetra-O- acetyl-beta-D-galactopyranosyl)-(1----4)-O-(2-acetamido-3,6-di-O-acetyl- 2- deoxy-beta-D-glucopyranosyl)-(1----4)]-3,6-di-O-benzyl-alpha-D-mannopyra nosyl trichloroacetimidate (5) and the corresponding fluoride 7, which, in turn, were prepared in 5 steps from allyl 3,6-di-O-benzyl-alpha-D-mannopyranoside in 35 and 22% overall yields, respectively. In model experiments, the key glycosyl donors 5 and 7 were also treated with the simple glycosyl acceptor 8-ethoxycarbonyloctanol, to give 8-methoxycarbonyloctyl O-beta-D-galactopyranosyl-(1----4)-O-(2-acetamido-2-deoxy-beta-D- glucopyranosyl)-(1----2)-O-[beta-D-galactopyranosyl-(1----4)-O-(2-acetam ido-2- deoxy-beta-D-glucopyranosyl)-(1----4)]-alpha (and beta)-D-mannopyranoside.
本文描述了七糖半抗原8 - 甲氧基羰基辛基O-β-D-吡喃半乳糖基-(1→4)-O-(2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基)-(1→2)-O-[β-D-吡喃半乳糖基-(1→4)-O-(2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基)-(1→4)]-O-α-D-吡喃甘露糖基-(1→3)-O-[α-D-吡喃甘露糖基-(1→6)]-β-D-吡喃甘露糖苷的合成方法，该方法使用了已知的、受保护的糖基受体8-乙氧基羰基辛基O-(2,3,4,6-四-O-苄基-α-D-吡喃甘露糖基)-(1→6)-2,4-二-O-苄基-β-D-吡喃甘露糖苷，以及关键的五糖基供体O-(2,3,4,6-四-O-乙酰基-β-D-吡喃半乳糖基)-(1→4)-O-(2-乙酰氨基-3,6-二-O-乙酰基-2-脱氧-β-D-吡喃葡萄糖基)-(1→2)-O-[(2,3,4,6-四-O-乙酰基-β-D-吡喃半乳糖基)-(1→4)-O-(2-乙酰氨基-3,6-二-O-乙酰基-2-脱氧-β-D-吡喃葡萄糖基)-(1→4)]-3,6-二-O-苄基-α-D-吡喃甘露糖基三氯乙酰亚胺酯(5)和相应的氟化物7，它们分别由烯丙基3,6-二-O-苄基-α-D-吡喃甘露糖苷经5步反应制备，总收率分别为35%和22%。在模型实验中，关键的糖基供体5和7也用简单的糖基受体8-乙氧基羰基辛醇处理，得到8-甲氧基羰基辛基O-β-D-吡喃半乳糖基-(1→4)-O-(2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基)-(1→2)-O-[β-D-吡喃半乳糖基-(1→4)-O-(2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基)-(1→4)]-α(和β)-D-吡喃甘露糖苷。
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