Synthetic approach toward antibiotic tunicamycins, 4.+ x-ray crystal structure analysis of a higher-carbon nitro sugar

Tetsuo Suami, Yoshimasa Fukuda, Junji Yamamoto, Yoshihiko Saito, Masatoki Ito, Shigeru Ohba

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

A higher-carbon carbohydrate, a derivative of undecose has been synthesized by the potassium fluoride-catalyzed addition of a nitro sugar to a sugar aldehyde. The addition of methyl 5-de-oxy-2,3-0-isopropylidene-5-nitro-6-D-ribofuranoside to methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-0-isopropylidene-a-D-galacto-dialdopyranoside-(1,5) yielded a single diastereomer of the nitro undecose derivative. The absolute configuration of two chiral centers of the derivative has been established by the X-ray crystal structure analysis.

Original languageEnglish
Pages (from-to)9-19
Number of pages11
JournalJournal of Carbohydrate Chemistry
Volume1
Issue number1
DOIs
Publication statusPublished - 1982 Jan 1

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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