Direct, microwave-assisted substitution of anomeric nitrate-esters

被引：8
|
作者：
Keith, D. Jamin [1 ]
Townsend, Steven D. [1 ,2 ]
机构：
[1] Vanderbilt Univ, Dept Chem, Nashville, TN 37235 USA
[2] Vanderbilt Univ, Inst Chem Biol, Nashville, TN 37232 USA
来源：
CARBOHYDRATE RESEARCH | 2017年 / 442卷
关键词：
Azido-nitration; Nitrate-ester; Hydrolysis; Glycosidation; Glycosylation Trichloroacetimidate; 2-AZIDO-2-DEOXY-D-GALACTOPYRANOSYL DERIVATIVES; GLYCOSYL DONORS; S-XANTHATES; AZIDONITRATION; GLYCALS;
D O I：
10.1016/j.carres.2017.02.005
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A series of carbohydrate 2-azido-1-nitrate-esters, protected at the C-3, C-4, and C-6 positions, were hydrolyzed thermally under reagent free conditions. This preliminary result was extended to direct exchange of the 1-nitrate-ester modality for alcohol, alkoxy, and azide coupling partners with minimal purification. While direct glycosylation of nitrate esters ultimately proved unsuccessful, we have demonstrated that an anomeric nitrate-ester can be converted directly to a trichloroacetimidate in a short and simple one-pot procedure, bypassing lower yielding two-step sequences. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码：20 / 24
页数：5
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