A ROUTE TO UNSATURATED SPIROKETALS FROM PHENYLTHIO HEX-2-ENOPYRANOSIDES VIA SEQUENTIAL ALKYLATION, ALLYLIC REARRANGEMENT AND INTRAMOLECULAR GLYCOSIDATION

被引:18
作者
GOMEZ, AM
VALVERDE, S
FRASERREID, B
机构
[1] INST QUIM ORGAN GEN,E-28006 MADRID,SPAIN
[2] DUKE UNIV,DEPT CHEM,PAUL M GROSS CHEM LAB,DURHAM,NC 27706
关键词
D O I
10.1039/c39910001207
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Alkylated phenylthio hex-2-enopyranosides readily undergo 1,3-phenylthio migration, and treatment of the resulting enol ether with N-iodosuccinimide gives an allyl-oxocarbenium ion which can be trapped intramolecularly by a suitably located hydroxy group to yield an unsaturated spiroketal.
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页码:1207 / 1208
页数:2
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