Catalytic Stereoselective Synthesis of β-Digitoxosides: Direct Synthesis of Digitoxin and C1′-epi-Digitoxin

被引：36
作者：
Baryal, Kedar N.
Adhikari, Surya
Zhu, Jianglong [1 ]
机构：
[1] Univ Toledo, Dept Chem, Toledo, OH 43606 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 24期
关键词：
S-BUT-3-YNYL THIOGLYCOSIDE DONORS; CARDIAC-GLYCOSIDES; GLYCOSYLATION; REARRANGEMENT; TRISACCHARIDE; DERIVATIVES; REACTIVITY; ANALOGS; GLYCALS; DIGOXIN;
D O I：
10.1021/jo4021419
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A mild and atom-economic rhenium(V)-catalyzed stereoselective synthesis of beta-D-digitoxosides from 6-deoxy-D-allals has been described. This beta-selective glycosylation was achieved probably because of the formation of corresponding alpha-digitoxosides disfavored by 1,3-diaxial interaction. In addition, this method has been successfully applied to the synthesis of digitoxin trisaccharide glycal for the direct synthesis of digitwdn and C1'-epi-digitoxin.
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收藏
页码：12469 / 12476
页数：8
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