INTRAMOLECULAR 1,3-DIPOLAR ADDITIONS IN 4-O-ALLYL PYRANOSIDE-6-NITRONES - AN APPROACH TO CHIRAL PYRANOPYRANS AND PYRANOOXEPANS

被引:38
作者
COLLINS, PM [1 ]
ASHWOOD, MS [1 ]
EDER, H [1 ]
WRIGHT, SHB [1 ]
KENNEDY, DJ [1 ]
机构
[1] MERCK SHARP & DOHME LTD, HODDESDON EN11 9BU, HERTS, ENGLAND
关键词
D O I
10.1016/S0040-4039(00)88914-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of the easily prepared 6-aldehydo-glucopyranoside allyl ether (5) with N-benzylhydroxylarnine gave nitrone (6), which underwent a 1,3-dipolar addition to the 4-O-allyl group giving after deprotection and hydrogenolysis the chiral pyrano-pyran (11) and the pyrano-oxepan (13). © 1990.
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页码:2055 / 2058
页数:4
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