C-6 allylated pyranosides for the synthesis of complex oxygenated tetrahydrofurans

被引：12

作者：

Seepersaud, M ^{[1
]}

Blumenstein, M ^{[1
]}

Mootoo, DR ^{[1
]}

机构：

[1] CUNY HUNTER COLL,DEPT CHEM,NEW YORK,NY 10021

来源：

TETRAHEDRON | 1997年 / 53卷 / 16期

关键词：

D O I：

10.1016/S0040-4020(97)00282-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The iodoetherification of C6 allylated D-pyranosides containing an allylic benzyloxy substituent, and their acyclic 5-hexen-, 1,2,4-triol analogs were performed. Pyranosides of R configuration at the allylic ether gave exclusively a syn,syn-2,5-dialkyi-3-oxy-tetrahydrofuran which is primed for elaboration into several classes of naturally occurring THF's. By comparison, the stereoselectivity for the non-pyranoside derivative was much lower. In the S series, the bias was opposite for the pyranoside vs, the non-pyranoside substrates, but the selectivity in both cases was low. (C) 1997 Elsevier Science Ltd.

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页码：5711 / 5724

页数：14

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