Synthesis of Potassium (2R)-2-O-α-D-Mannopyranosyl-(1→2)-α-D-glucopyranosyl-2,3-dihydroxypropanoate: A Naturally Compatible Solute

被引：4

作者：

Lourenco, Eva C. ^{[1
]}

Rita Ventura, M. ^{[1
]}

机构：

[1] Univ Nova Lisboa, Inst Tecnol Quim & Biol, P-2780901 Oeiras, Portugal

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 33期

关键词：

Glycosylation; Hypersolutes; Natural products; Thioglycosides; Solid-phase synthesis; SOLID-PHASE SYNTHESIS; GLYCOSYL;

D O I：

10.1002/ejoc.201100934

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An expedient synthesis of the potassium salt of (2R)-2-O-alpha-D-mannopyranosyl-(1 -> 2)-alpha-D-glucopyranosyl-2,3-dihydroxypropanoic acid (MGG)-a recently isolated, rare, compatible solute-was accomplished. A bis-acetal-protected thioglucoside, 6-OTBDPS, with a 2-OH group was used as the acceptor in the first glycosylation reaction with tetraacetylman-nosyl trichloroacetimidate, and as the donor in the glycosylation reaction with the glycerate derivative. The a anomer was the only product of both glycosylation reactions, as expected for the formation of the a-mannoside. The formation of the 1,2-cis glucoside was more challenging.

引用

页码：6698 / 6703

页数：6

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