Synthesis of 6-amino-3-5-deoxyinositol 1-phosphates via (1R,2R,4R,6S)-1,6-Epoxy-2,4-bis-benzyloxycyclohexane aminolysis in aqueous ytterbium triflate solution

被引：19

作者：

Beaton, M

Gani, D

机构：

[1] Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland

[2] Univ St Andrews, Ctr Biomol Sci, St Andrews KY16 9ST, Fife, Scotland

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 46期

关键词：

D O I：

10.1016/S0040-4039(98)01909-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(1R,2R,4R,6S)-1,6-Epoxy-2,4-bis-benzyloxycyclohexane was prepared from (-)-quinic acid and this, and cyclohexene oxide, were treated with various N-nucleophiles under a variety of conditions. In aqueous solution containing catalytic amounts of ytterbium (III) triflate, ammonia and alkylamines reacted smoothly to give the required trans-1,2-amino alcohols in quantitative recovery. Conversion of the 6-amino-2,4-bis-benzyloxycyclohexan-1-ols to 6-amino-1,2,4-trihydroxycyclohexane 1-phosphates, probes for the mechanism of inositol monophosphatase, was achieved in good overall yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

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收藏

页码：8549 / 8552

页数：4

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