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

A new process suitable for large scale synthesis of the antitumor‐antiviral agent, 2‐β‐D‐ribofuranosyl‐4‐selenazolecarboxamide (selenazofurin, 1), has been developed. Thus, 1‐O‐acetyl‐2,3,5‐tri‐O‐benzoyl‐β‐D‐ribofuranose (3) was converted with cyanotrimethylsilane and stannic chloride to the crystalline 2,5‐anhydro‐3,4,6‐tri‐O‐benzoyl‐β‐D‐allononitrile (4) without chromatography. Cyanosugar 4 in ethanol was treated with hydrogen selenide gas to afford stereospecifically the unstable 2,5‐anhydro‐3,4,6‐tri‐O‐benzoyl‐β‐D‐allonoselenoamide (5) which was converted in situ by ethyl bromopyruvate to the stable ethyl 2‐(2,3,5‐tri‐O‐benzoyl‐β‐D‐ribofuranosyl)‐4‐selenazolecarboxylate (6). Selenazole ethyl ester 6 was deprotected with sodium methoxide affording methyl 2‐β‐D‐ribofuranosyl‐4‐selenazolecarboxylate (7) which was aminated with ammonia to provide selenazofurin (1) or with other amines to provide N‐substituted selenazofurin amides.

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Collins¹

1998

Dictionary of Carbohydrates

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

Cited by 9 publications

References 14 publications

ChemInform Abstract: IMPROVED SYNTHESIS OF 2,5‐ANHYDRO‐D‐ALLONONITRILE

ChemInform Abstract: IMPROVED SYNTHESIS OF 2,5‐ANHYDRO‐D‐ALLONONITRILE

A synthesis of 2‐β‐D‐ribofuranosyl‐4‐selenazolecarboxamide (selenazofurin) and certain N‐substituted amide derivatives suitable for large scale syntheses

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