Improved synthesis of 2,5-anhydro-d-allononitrile

Document Type

Article

Publication Date

4-16-1983

Department

Department of Chemical Engineering; Department of Chemistry

Abstract

Two types of mixed ester of β-d-ribofuranose were synthesized. The first had the same groups attached to O-1, 2, and 3, and the second had the same groups attached to O-2, 3, and 5. The three esters obtained in the highest yields, starting from d-ribose, were then converted into the halides and nitriles. Of the esters studied, the best suited for conversion into the nitrile was 1-O-acetyl-2,3,5-tri-O-p-toluyl-β-d-ribofuranose, which afforded 2,5-anhydro-3,4,6-tri-O-p-toluyl-d-allononitrile in 60% yield.

Publication Title

Carbohydrate Research

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