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

  1. Get@NRC: Synthesis of 2-amino-2-deoxy-D-talose and 2-amino-2-deoxy-D-galactose (Opens in a new window)
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Journal titleCanadian Journal of Chemistry
Pages24812484; # of pages: 4
AbstractTreatment 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
AffiliationNational Research Council Canada; NRC Institute for Biological Sciences
Peer reviewedNo
NRC numberPERRY1968A
NPARC number9381357
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Record identifier2f099136-c257-486b-ab82-8f9fac3062d4
Record created2009-07-10
Record modified2016-05-09
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