Stereoselective Synthesis of 2-(β-C-Glycosyl)glycals: Access to Unusual β-C-Glycosides from 3-Deoxyglycals

被引：12
|
作者：
Reddy, Gadi Madhusudhan [1 ]
Rao, Boddu Uma Maheswara [1 ]
Sridhar, Perali Ramu [1 ]
机构：
[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 07期
关键词：
HYDRIDE REDUCTIVE REARRANGEMENT; CONFORMATIONAL-ANALYSIS; GLYCALS; GLYCOSYLATION; STEREOCHEMISTRY; ISOMERIZATION; DISACCHARIDES; ROUTE;
D O I：
10.1021/acs.joc.5b02879
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel method for the highly stereoselective synthesis of beta-(1 -> 2)-C-saccharides employing 3-deoxy- and 3-C-branched glycals as hermaphroditic substrates is revealed. The generality of the C-C bond formation reaction between the two sugar units is evaluated. The developed methodology is successfully applied to the synthesis of biologically significant subunits that are present in various natural products, which include mixed C-disaccharides with adjacent THP-THF rings, C-aryl glycosides, and highly functionalized beta-C-glycosides.
引用
收藏
页码：2782 / 2793
页数：12
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