TMSCl as a mild and effective source of acidic catalysis in Fischer glycosidation and use of propargyl glycoside for anomeric protection

Minoru Izumi, Koichi Fukase, Shoichi Kusumoto

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Practical Fischer glycosidation was effected at room temperature or 60°C by using 5 to 10 equiv. of TMSCl. The anomeric propargyl group formed by this method was found to be a versatile new protecting group, being stable in neat TFA but readily cleaved by treatment with Co2(CO)8 and TFA in CH2Cl2 via the formation of an alkyne-Co complex.

Original languageEnglish
Pages (from-to)211-214
Number of pages4
JournalBioscience, Biotechnology and Biochemistry
Volume66
Issue number1
Publication statusPublished - Jan 2002
Externally publishedYes

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alkynes
Glycosides
Alkynes
Catalysis
catalytic activity
glycosides
ambient temperature
Temperature
methodology

Keywords

  • Acid catalyst
  • Fischer glycosidation
  • Protective group
  • TMSCl

ASJC Scopus subject areas

  • Food Science
  • Applied Microbiology and Biotechnology
  • Chemistry (miscellaneous)
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Biotechnology
  • Bioengineering

Cite this

TMSCl as a mild and effective source of acidic catalysis in Fischer glycosidation and use of propargyl glycoside for anomeric protection. / Izumi, Minoru; Fukase, Koichi; Kusumoto, Shoichi.

In: Bioscience, Biotechnology and Biochemistry, Vol. 66, No. 1, 01.2002, p. 211-214.

Research output: Contribution to journalArticle

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