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3-O-(α-D-吡喃葡萄糖基)-7-O-(L-甘油-α-D-甘露庚吡喃糖基)-L-甘油-α-D-甘露庚吡喃糖苷甲酯的合成

Synthesis of methyl 3-O-(alpha-D-glucopyranosyl)-7-O-(L-glycero-alpha-D- manno-heptopyranosyl)-L-glycero-alpha-D-manno-heptopyranoside.

作者信息

Garegg P J, Oscarson S, Szönyi M

机构信息

Department of Organic Chemistry, Arrhenius Laboratory, University of Stockholm, Sweden.

出版信息

Carbohydr Res. 1990 Sep 19;205:125-32. doi: 10.1016/0008-6215(90)80133-n.

Abstract

The title trisaccharide glycoside, which is related to part of the core region of the lipopolysaccharide from Salmonella, and the disaccharide glycosides methyl 3-O-alpha-D-glucopyranosyl-L-glycero-alpha-D-manno-heptopyranoside and methyl 7-O-L-glycero-alpha-D-manno-heptopyranosyl-L-glycero-alpha-D-manno- heptopyranoside have been synthesised. Methyl 2,3,4-tri-O-benzyl-L-glycero-alpha-D-manno- heptopyranoside, obtained via a one-carbon elongation at C-6 of methyl 2,3,4-tri-O-benzyl-alpha-D-manno- hexodialdo-1,5-pyranoside, was used as precursor both for the heptosyl donor and acceptor.

摘要

已合成了与沙门氏菌脂多糖核心区域部分相关的标题三糖糖苷,以及二糖糖苷3-O-α-D-吡喃葡萄糖基-L-甘油-α-D-甘露庚糖苷甲酯和7-O-L-甘油-α-D-甘露庚糖基-L-甘油-α-D-甘露庚糖苷甲酯。通过在2,3,4-三-O-苄基-α-D-甘露己二醛-1,5-吡喃糖苷的C-6位进行单碳延长得到的2,3,4-三-O-苄基-L-甘油-α-D-甘露庚糖苷甲酯,被用作庚糖供体和受体的前体。

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