L-Rhamnosylation: The Solvent is the Solution

被引：26

作者：

Elferink, Hidde ^{[2
]}

Pedersen, Christian Marcus ^{[1
]}

机构：

[1] Univ Copenhagen, Dept Chem, Univ Pk 5, DK-2100 Copenhagen, Denmark

[2] Radboud Univ Nijmegen, Inst Mol & Mat, Heyendaaleweg 135, Nijmegen, Netherlands

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 01期

关键词：

Rhamnosylation; Glycosylation; Stereoselectivity; Reactivity; Solvent effects; BETA-L-RHAMNOPYRANOSIDES; CONFORMATIONAL EQUILIBRIA; STEREOSELECTIVE-SYNTHESIS; GLYCOSYLATION REACTIONS; D-MANNOPYRANOSIDES; PROTECTING GROUPS; IONS; GLYCOSIDES; OLIGOSACCHARIDE; ACETALS;

D O I：

10.1002/ejoc.201601355

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein we present a systematic study of L-rhamnosylation. The influence of protective groups, reactivity, solvents and glycosylation method, i.e. catalytic versus promoted glycosylation, are studied. It was found that the selectivity can be controlled to a large extend, by varying these parameters and hence the same donor can give both anomers. A reversal of the influence of the participating solvents is observed, and hence ethereal solvents increase the beta selectivity, whereas nitrile solvents give almost exclusive alpha-selectively.

引用

页码：53 / 59

页数：7

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