Synthesis and elucidation of absolute stereochemistry of salaprinol, another thiosugar sulfonium sulfate from the ayurvedic traditional medicine Salacia prinoides

被引：42

作者：

Tanabe, Genzoh ^{[1
]}

Sakano, Mika ^{[1
]}

Minematsu, Toshie ^{[1
]}

Matusda, Hisashi ^{[2
]}

Yoshikawa, Masayuki ^{[2
]}

Muraoka, Osamu ^{[1
]}

机构：

[1] Kinki Univ, Sch Pharm, Osaka 5778502, Japan

[2] Kyoto Pharmaceut Univ, Yamashina Ku, Kyoto 6078412, Japan

来源：

TETRAHEDRON | 2008年 / 64卷 / 43期

基金：

日本学术振兴会;

关键词：

Salaprionol; epi-Salaprinol; alpha-Glucosidase inhibitor; Sulfonium sulfate; Salacia prinoides;

D O I：

10.1016/j.tet.2008.08.010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis and elucidation of absolute stereochemistry of salaprinol (3) isolated from the root and sterns of Salacia prinoides, which has been used for the treatment of diabetes in India, Sri Lanka, and Southeast Asia countries, is described. Compound 3 and its 2'-epimer, epi-salaprinol (epi-3) were synthesized via the coupling reaction of a cyclic sulfate, 2-O-benzylglycerol 1,3-cyclic sulfate (S), with a thiosugar, 1,4-dideoxy-1,4-epithio-D-arabinitol (6), as the key reaction, and S configuration of the asymmetric center in the side chain of 3 was elucidated by the X-ray crystallographic analysis. (C) 2008 Published by Elsevier Ltd.

引用

页码：10080 / 10086

页数：7