An Improved Method for Synthesizing Antennary β-D-Mannopyranosyl Disaccharide Units.
An Improved Method for Synthesizing Antennary β-D-Mannopyranosyl Disaccharide Units.
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一种合成触角 β-D-吡喃甘露糖基二糖单元的改进方法。
DOI：
10.1002/chin.200506179
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发表时间：
2005
期刊：
影响因子：
--
通讯作者：
Y. Takai
中科院分区：
文献类型：
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作者：
Ken;S. Akai;Akira Yoshitomo;Y. Takai
摘要研究了由β- d -半乳糖吡喃二糖合成天线型β- d -甘露吡喃二糖时烯丙基经烯丙氧羰基间接保护羟基的方法的优点。研究了O -[β- d -半乳糖基]-(1-4)-3,6-二- O -苄基-2-脱氧-2- N -邻苯二胺-β- d -葡萄糖吡喃苷在C-2′和C-4′上同时发生双ns2亲核取代的区域选择性烯丙基羰基化和转化反应，并与直接烯丙基化方法进行了比较。采用该间接法，以52%的收率获得了所需的具有适当保护基团的β- d -甘露吡喃基二糖。相比之下，用甲基O -（β- d -半乳糖酰基）二糖直接烯丙基化的方法只能得到相应的β- d -甘露酰基二糖，收率只有7.5%。
Abstract The merits of an indirect protecting method for hydroxyl groups using allyl groups via allyloxycarbonyl groups in the synthesis of antennary β- d -mannopyranosyl disaccharides from β- d -galactopyranosyl disaccharides were studied. Regioselective allyloxycarbonylation and conversion reactions involving simultaneous double S N 2 nucleophilic substitution at C-2′ and C-4′ of benzyl O -[β- d -galactopyranosyl]-(1-4)-3,6-di- O -benzyl-2-deoxy-2- N -phthalimido-β- d -glucopyranoside were examined for comparison with the direct allylation method. The required β- d -mannopyranosyl disaccharide having proper protecting groups was obtained using this indirect method in 52% yield. In contrast, the reported direct allylation method using methyl O -(β- d -galactopyranosyl) disaccharide gave the corresponding β- d -mannopyranosyl disaccharide in only 7.5% yield.