Synthesis of di-branched heptasaccharide by one-pot glycosylation using seven independent building blocks

Hiroshi Tanaka, Masaatsu Adachi, Hirokazu Tsukamoto, Takeji Ikeda, Haruo Yamada, Takashi Takahashi

Research output: Contribution to journalArticle

74 Citations (Scopus)

Abstract

(Equation presented) We describe an efficient synthesis of di-branched heptasaccharide 1 having phytoalexin elicitor activity in soybeans by one-pot glycosylation. The synthesis involves chemo-and regioselective sequential six-step glycosylations using seven independent building blocks and sequential removal of acyl-and benzyl ether-type protecting groups. The coupling of seven building blocks requires only four chemoselective activitable leaving groups of glycosyl donors. Both the glycosylation and deprotection reactions can be achieved utilizing a parallel manual synthesizer.

Original languageEnglish
Pages (from-to)4213-4216
Number of pages4
JournalOrganic letters
Volume4
Issue number24
DOIs
Publication statusPublished - 2002 Nov 28

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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