A Facile Synthesis of Acyclo-C-nucleoside Analogues from 2(3)-Formylglycals [1]

Abstract

The reaction of 2(3)-formylglycals with malononitrile afforded push-pull butadienes with a sugar moiety. The treatment of these branched-chain sugars with ammonia yielded nicotinonitrile acyclo-C-nucleosides. Furthermore, a one step ring transformation of 2(3)-formylglycals with N-aryl-acetoacetanilides to give pyridone acyclo-C-nucleosides is described.

Key words

aldehydes - nucleosides - carbohydrates - formylglycals - push-pull butadienes

1

Presented at the XIX^th International Carbohydrate Symposium, San Diego, USA, 1998.

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1

Presented at the XIX^th International Carbohydrate Symposium, San Diego, USA, 1998.