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Syntheses of methyl N-benzoylacosaminide and methyl N-(benzyloxyoxalyl)-daunosaminide from (S)-ethyl 3-hudroxybutyrate

✍ Scribed by Deok-Chan Ha; David J. Hart

Book ID: 104227867
Publisher: Elsevier Science
Year: 1987
Tongue: French
Weight: 198 KB
Volume: 28
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)96544-4

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✦ Synopsis

A formal total synthesis of acosamine and the preparation of N-acylated daunosamine derivative 4 from a common intermediate (13) is described. Acosamine (1)2 and daunosamine (2)3 are 2,3,6-trideoxyaminohexoses found as structural subunits of glycosidic and polysaccharide antibiotics. These aminosaccharides have been the objectives of numerous synthetic studies, largely because of their appearance as components of anthracycline antibiotics and derivatives thereof.4 This letter describes enantioselective syntheses of methyl N-benzoylacosaminide (3) and methyl N-(benzyloxyoxalyl)daunosaminide (4) from (S)-ethyl 3-hydroxybutyrate (5).

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