SYNTHESES OF VALIDAMINE, EPI-VALIDAMINE, AND VALIENAMINE, THREE OPTICALLY ACTIVE PSEUDO-AMINO-SUGARS, FROM D-GLUCOSE

SYNTHESES OF VALIDAMINE, EPI-VALIDAMINE, AND VALIENAMINE, THREE OPTICALLY ACTIVE PSEUDO-AMINO-SUGARS, FROM D-GLUCOSE

Using as a key reaction a Michael-type addition reaction to nitroolefins or a substitution reaction for an acetoxyl residue at the β-position of the nitro group in pseudo-nitro-sugar, three optically active pseudo-amino-sugars: validamine, epi-validamine, and valienamine, were synthesized from D-glu...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1988/10/25, Vol.36(10), pp.4236-4239
Hauptverfasser: Yoshikawa, Masayuki, Cha, Bae Cheon, Okaichi, Yoshihiko, Takinami, Yoshihiko, Yokokawa, Yoshihiro, Kitagawa, Isao
Format: Artikel
Sprache:eng
Schlagworte:
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
epivalidamine
Exact sciences and technology
Michael-type addition
Organic chemistry
Preparations and properties
pseudo-amino-sugar optically active
pseudo-amino-sugar synthesis
pseudo-nitro-sugar
validamine
valienamine
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Zusammenfassung:Using as a key reaction a Michael-type addition reaction to nitroolefins or a substitution reaction for an acetoxyl residue at the β-position of the nitro group in pseudo-nitro-sugar, three optically active pseudo-amino-sugars: validamine, epi-validamine, and valienamine, were synthesized from D-glucose.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.36.4236