The Journal of Organic Chemistry

Routes to C-glycopyranosides via sigmatropic rearrangements

DB Tulshian, B Fraser-Reid

Index: Tulshian, Deen Bhandu; Fraser-Reid, Bert Journal of Organic Chemistry, 1984 , vol. 49, # 3 p. 518 - 522

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Citation Number: 66

Abstract

Claisen rearrangements have been applied to 1, 5-anhydro-4, 6-0-benzylidene-1, 2-dideoxy- ~-ri~ o-hex-l-enitol (1). The classical procedure succeeds, but the overall process is unsatisfactory because of the low conversion to the vinyl ether intermediate. Best results were had with the Eschenmoser procedure, and the NJV-di-methyl (hex-2'-enopyranosyl) acetamide produced, 7, can be converted into the corresponding ethyl ester. However ...