Simple formylacetal (CH2) as a novel linker for saccharide synthesis on soluble-polymer support

Masato Oikawa, Tatsushi Tanaka, Shoichi Kusumoto, Makoto Sasaki

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

Described herein is a new formylacetal (CH2) linker for immobilization of small molecules onto a soluble-polymer support, poly(ethylene glycol) ω-monomethyl ether (MPEG), and its application to saccharide synthesis. This small linker allows immobilization of a hindered hydroxy group such as the 4-hydroxy group of glucose onto MPEG. The linker is stable under several reaction conditions including glycosylation. Removal of this support was found to be achieved through cleavage of the CH2 linker either by a Lewis acid (TMSI or Ce(OTf)x) or a Brønsted acid (trifluoroacetic acid) in moderate to good yields. In combination with solid acid catalyst, simpler operations became possible during the working-up and purification processes.

Original languageEnglish
Pages (from-to)787-790
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number4
DOIs
Publication statusPublished - 2004 Jan 19

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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