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1970•Journal of the Chemical Society D Chemical CommunicationsRequires access

The nitrous acid deamination of methyl 4-amino-4-deoxy-2,3-O-isopropylidene-α- L -talo- and -mannopyranosides

A. K. AL‐RADHI, J. S. Brimacombe, L. C. N. TUCKER

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Abstract

Deamination of the L-talo-amine (I) with sodium nitrite in 90% acetic acid afforded the L-mannopyranosides (III) and (IV), whereas similar deamination of the L-manno-amine (V) gave (III), (IV), and rearrangement products (VIII) and (IX) possessing the D-allo-configuration.

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What this paper is about

Deamination of the L-talo-amine (I) with sodium nitrite in 90% acetic acid afforded the L-mannopyranosides (III) and (IV), whereas similar deamination of the L-manno-amine (V) gave (III), (IV), and rearrangement products (VIII) and (IX) possessing the D-allo-configuration.

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Available abstract

Deamination of the L-talo-amine (I) with sodium nitrite in 90% acetic acid afforded the L-mannopyranosides (III) and (IV), whereas similar deamination of the L-manno-amine (V) gave (III), (IV), and rearrangement products (VIII) and (IX) possessing the D-allo-configuration.

Key concepts: Deamination, Chemistry, Nitrous acid, Amine gas treating, Sodium nitrite, Medicinal chemistry, Oxidative deamination, Acetic acid

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The nitrous acid deamination of methyl 4-amino-4-deoxy-2,3-O-isopropylidene-α- L -talo- and -mannopyranosides — Research Paper | ScholarLens