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Synthesis of 2-amino-2-deoxy-D-talose and 2-amino-2-deoxy-D-galactose

From National Research Council Canada

DOIResolve DOI: https://doi.org/10.1139/v68-407
AuthorSearch for: 1; Search for: 1
Affiliation
  1. National Research Council of Canada. NRC Institute for Biological Sciences
FormatText, Article
Abstract
Treatment of D-lyxose with nitromethane in the presence of sodium methoxide gave 1-deoxy-1-nitro-D-galactitol which, after conversion to 2,3,4,5,6-penta-O-acetyl-1-deoxy-1-nitro-D-galactitol, reacted with saturated methanolic ammonia solution to yield 2-acetamido-1,2-dideoxy-1-nitro-D-talitol and 2-acetamido-1,2-dideoxy-1-nitro-D-galactitol. 2-Acetamido-1,2-dideoxy-1-nitro-D-talitol and 2-acetamido-1,2-dideoxy-1-nitro-D-galactitol were converted by a modified Nef reaction to 2-acetamido-2-deoxy-D-talose and 2-acetamido-2-deoxy-D-galactose which on hydrolysis with hydrochloric acid afforded 2-amino-2-deoxy-D-talose hydrochloride and 2-amino-2-deoxy-D-galactose hydrochloride. The properties and derivatives of the aminoglycoses are described.
Publication date
In
  • Canadian Journal of Chemistry 46, no. 15 (1968): 2481–2484.
LanguageEnglish
NRC numberPERRY1968A
NRCC 10134
NPARC number9381357
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Record identifier2f099136-c257-486b-ab82-8f9fac3062d4
Record created2009-07-10
Record modified2020-03-12
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