Organic & biomolecular chemistry

Synthesis of 4-deoxy-4-nitrosialic acid

I Hemeon, AJ Bennet

Index: Hemeon, Ivan; Bennet, Andrew J. Organic and Biomolecular Chemistry, 2006 , vol. 4, # 15 p. 2986 - 2992

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Citation Number: 5

Abstract

The synthesis of 4-deoxy-4-nitrosialic acid (3, 4, 5-trideoxy-4-nitro-D-glycero-β-D-galacto- non-2-ulopyranosonic acid, 5), was completed in seven steps starting from D-arabinose. Coupling of the 6-carbon fragment, 2-acetamido-1, 2-dideoxy-1-nitro-D-mannitol (6) with ethyl α-(bromomethyl) acrylate afforded a 2: 1 mixture of ethyl 5-acetamido-2, 3, 4, 5- tetradeoxy-2-methylene-4-nitro-D-glycero-D-galacto-nononate (9a-S) and ethyl 5- ...

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