碳水化合物化学中用于保护的烯丙基。17. 丙基O-(3,6-二-O-甲基-β-D-吡喃葡萄糖基)-(1→4)-O-(2,3-二-O-甲基-α-L-鼠李吡喃糖基)-(1→2)-3-O-甲基-α-L-鼠李吡喃糖苷的合成：麻风分枝杆菌主要血清学活性糖脂的寡糖部分。

The allyl group for protection in carbohydrate chemistry. 17. Synthesis of propyl O-(3,6-di-O-methyl-beta-D-glucopyranosyl)-(1----4)-O-(2,3- di-O-methyl-alpha-L-rhamnopyranosyl)-(1----2)-3-O-methyl-alpha- L-rhamnopyranoside: the oligosaccharide portion of the major serologically active glycolipid from Mycobacterium leprae.

作者信息

Gigg J, Gigg R, Payne S, Conant R

出版信息

Chem Phys Lipids. 1985 Sep;38(3):299-307. doi: 10.1016/0009-3084(85)90023-4.

Abstract

Allyl 4-O-benzyl-alpha-L-rhamnopyranoside was converted into allyl 4-O-benzyl-3-O-methyl-alpha-L-rhamnopyranoside and this was condensed with 2,3,4-tri-O-acetyl-alpha-L-rhamnopyranosyl chloride to give a disaccharide derivative which was converted into allyl 4-O-benzyl-2-O-(2,3-O-isopropylidene-alpha-L-rhamnopyranosyl)-3-O-methyl -alpha- L-rhamnopyranoside. This disaccharide derivative was condensed with 2,4-di-O-acetyl-3,6-di-O-methyl-alpha-D-glucopyranosyl chloride to give a trisaccharide derivative which was converted into the title compound. This compound represents the oligosaccharide portion of the major serologically active glycolipid from Mycobacterium leprae which is required to prepare a synthetic diagnostic agent for leprosy infection at an early stage and to investigate the specificities of monoclonal antibodies directed towards the glycolipid.

摘要

烯丙基4-O-苄基-α-L-鼠李吡喃糖苷被转化为烯丙基4-O-苄基-3-O-甲基-α-L-鼠李吡喃糖苷，然后将其与2,3,4-三-O-乙酰基-α-L-鼠李吡喃糖基氯缩合，得到一种二糖衍生物，该二糖衍生物被转化为烯丙基4-O-苄基-2-O-(2,3-O-异亚丙基-α-L-鼠李吡喃糖基)-3-O-甲基-α-L-鼠李吡喃糖苷。该二糖衍生物与2,4-二-O-乙酰基-3,6-二-O-甲基-α-D-吡喃葡萄糖基氯缩合，得到一种三糖衍生物，该三糖衍生物被转化为标题化合物。该化合物代表麻风分枝杆菌主要血清学活性糖脂的寡糖部分，这是制备麻风病早期感染的合成诊断剂以及研究针对该糖脂的单克隆抗体特异性所必需的。