Synthesis of methyl (methyl d- and l-idopyranosid) uronates from myo-inositol

Noritaka Chida, Eriko Yamada, Seiichiro Ogawa

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

Methyl (methyl α-D- (9a), α-L- (9b), β-D- (10a), and β-L- (10b) idopyranosid)uronates were synthesized from myo-inositol. Baeyer-Villiger oxidation of the optically resolved inosose derivatives (3a and 3b) proceeded regioselectively to afford 4a and 4b in high yields, respectively. Ring-opening of the 7-membered hemiacetal-lactones (4a and 4b) with acid and subsequent deprotection gave the title compounds.

Original languageEnglish
Pages (from-to)555-570
Number of pages16
JournalJournal of Carbohydrate Chemistry
Volume7
Issue number3
DOIs
Publication statusPublished - 1988

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Lactones
Inositol
Derivatives
Oxidation
Acids
inosose

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

Cite this

Synthesis of methyl (methyl d- and l-idopyranosid) uronates from myo-inositol. / Chida, Noritaka; Yamada, Eriko; Ogawa, Seiichiro.

In: Journal of Carbohydrate Chemistry, Vol. 7, No. 3, 1988, p. 555-570.

Research output: Contribution to journalArticle

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