STEREOSELECTIVE CONVERSION OF D-GLUCURONOLACTONE INTO PSEUDO-SUGAR - SYNTHESES OF PSEUDO-ALPHA-D-GLUCOPYRANOSE, PSEUDO-BETA-D-GLUCOPYRANOSE, AND VALIDAMINE

被引：28

作者：

YOSHIKAWA, M ^{[1
]}

MURAKAMI, N ^{[1
]}

YOKOKAWA, Y ^{[1
]}

INOUE, Y ^{[1
]}

KURODA, Y ^{[1
]}

KITAGAWA, I ^{[1
]}

机构：

[1] OSAKA UNIV,FAC PHARMACEUT SCI,SUITA,OSAKA 565,JAPAN

来源：

TETRAHEDRON | 1994年 / 50卷 / 32期

关键词：

D O I：

10.1016/S0040-4020(01)85530-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two optically active pseudo-sugars, pseudo-alpha-D-glucopyranose (12) and pseudo-beta-D-glucopyranose (13), were synthesized from D-glucuronolactone in favorable overall yields by using a stereoselective nitromethane addition reaction and a reductive elimination of an ethoxyethoxyl moiety with NaBH4 as key steps. Furthermore, a biologically active pseudo-aminosugar, validamine (18) was efficiently synthesized via a substitution reaction for an acetoxyl group at the beta-position of nitro group in a nitrocyclitol derivative (14) which was prepared from a synthetic intermediate (9) of pseudo-D-glucopyranoses (12, 13).

引用

页码：9619 / 9628

页数：10

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