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Stereoselective conversion of D-glucuronolactone into pseudo-sugar: Syntheses of pseudo -α-D-glucopyranose, pseudo-β-D-glucopyranose, and validamine

✍ Scribed by Masayuki Yoshikawa; Nobutoshi Murakami; Yoshihiro Yokokawa; Yasunao Inoue; Yasuyuki Kuroda; Isao Kitagawa

Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 799 KB
Volume: 50
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)85530-7

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✦ Synopsis

TWO optically active pseudo-sugars, pseudo-a-D-gluse (12) and pse&~Bglucqyra~~~ (13). were synthesized from D-glucuronolactonc in favorable overall yields by using a stereoselective nimunethane addition reaction and a reductive elimination of an ethoxyethoxyl moiety with NaBH4 as key steps. Furthermore, a biologically active pseudo-aminosugar, validamine (18) was efficiently synthesii via a substitution reaction for an acetoxyl group at the fl-position of nitro group in a nitrocyclitol derivative (14) which was prepared from a synthetic intermediate (9) of psclcdo-D-glucopyranoses (12.13).

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