Branched-chain Sugars. XI. Synthesis of 2,3,6-Trideoxy-3-C,4-O-dimethyl-3-nitro-D-arabino-hexopyranose (D-Evernitrose)

2,3,6-Trideoxy-3-C, 4-O-dimethyl-3-nitro-D-arabino-hexopyranose was synthesized by the oxidation of methyl α-glycoside of the corresponding 3-amino derivative with m-chloroperbenzoic acid followed by hydrolysis. The 3-amino derivative was synthesized from methyl 4,6-O-benzylidene-2-deoxy-α-D-erythro...

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Published inBulletin of the Chemical Society of Japan Vol. 51; no. 7; pp. 2064 - 2067
Main Authors Yoshimura, Juji, Matsuzawa, Masafumi, Funabashi, Masuo
Format Journal Article
LanguageEnglish
Published Tokyo The Chemical Society of Japan 01.07.1978
Chemical Society of Japan
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Summary:2,3,6-Trideoxy-3-C, 4-O-dimethyl-3-nitro-D-arabino-hexopyranose was synthesized by the oxidation of methyl α-glycoside of the corresponding 3-amino derivative with m-chloroperbenzoic acid followed by hydrolysis. The 3-amino derivative was synthesized from methyl 4,6-O-benzylidene-2-deoxy-α-D-erythro-hexopyranosid-3-ulose by introduction of the amino-branching function according to the method of Bourgeois, followed by 6-deoxygenation and 4-O-methylation.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.51.2064