THE 1ST EXAMPLE OF C-GLUCOPYRANOSIDES

被引：5

作者：

ALLEVI, P ^{[1
]}

ANASTASIA, M ^{[1
]}

CIUFFREDA, P ^{[1
]}

FIECCHI, A ^{[1
]}

SCALA, A ^{[1
]}

机构：

[1] UNIV MILAN,FAC MED,DEPT MED CHEM & BIOCHEM,VIA SALDINI 50,I-20133 MILAN,ITALY

来源：

CHEMISTRY AND PHYSICS OF LIPIDS | 1990年 / 53卷 / 2-3期

关键词：

C-glucopyranosides; C-glucosidation; C-glucosides; steroidic C-glucosides; steroids;

D O I：

10.1016/0009-3084(90)90048-V

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：

Treatment of 2,3,4,6-tetra-O-benzyl-d-glucopyranose trifluoroacetate with the appropriate steroid afforded the starting C-glycopyranosides for the synthesis of 1-(5α-cholestan-3β-yl)-2-β-d-glucopyranosyl-1-ethanone (IV), 1-(5α-cholestan-3β-yl)-2-β-d-glucopyranosylethane (VI), 3β-hydroxy-16β-(β-d-glucopyranosyl)-5α-androstan-17-one (X), 3β-hydroxy-21-β-d-glucopyranosyl-5-pregnen-20-one (XIV), 2-β-d-glucopyranosyl-1,3,5-estratriene-3,17β-diol (XVI), 2-β-d-glucopyranosyl-3-hydroxy-1,3,5-estratrien-17-on (XVIII). These compound represent the first examples of steroidic C-glucosides, a new class of compounds useful as possible enzyme inhibitiors. Unambiguous determination of the structure of all compounds was obtained by means of the 1HNMR spectra at 500 MHz or by chemical transformations. © 1990.

引用

页码：219 / 230

页数：12

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