Widely applicable deprotection method of 2,2,2-trichloroethoxycarbonyl (Troc) group using tetrabutylammonium fluoride

Cheng Yuan Huang, Ning Wang, Katsumasa Fujiki, Yuji Otsuka, Masao Akamatsu, Yukari Fujimoto, Koichi Fukase

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

The N-Troc (2,2,2-trichloroethoxycarbonyl) groups in glucosamine and muramic acid derivatives were removed by treatment with tetrabutylammonium fluoride (TBAF) under mild conditions. The use of Troc protection for the amino group in aminosugars such as glucosamine is increasing the importance for selective and efficient glycosylation, and the cleavage method described here will expand the available opportunities for using the Troc group in the preparation of a variety of glycans. This cleavage is especially advantageous for compounds that are labile or may be decomposed under acidic conditions, strong basic conditions, or reductive conditions.

Original languageEnglish
Pages (from-to)289-298
Number of pages10
JournalJournal of Carbohydrate Chemistry
Volume29
Issue number6
DOIs
Publication statusPublished - 2010 Aug
Externally publishedYes

Fingerprint

Glucosamine
Muramic Acids
Glycosylation
Polysaccharides
Derivatives
tetrabutylammonium

Keywords

  • 2,2,2-Trichloroethoxycarbonyl group
  • Deprotection
  • Glucosamine
  • Tetrabutylammonium fluoride

ASJC Scopus subject areas

  • Organic Chemistry
  • Biochemistry

Cite this

Widely applicable deprotection method of 2,2,2-trichloroethoxycarbonyl (Troc) group using tetrabutylammonium fluoride. / Huang, Cheng Yuan; Wang, Ning; Fujiki, Katsumasa; Otsuka, Yuji; Akamatsu, Masao; Fujimoto, Yukari; Fukase, Koichi.

In: Journal of Carbohydrate Chemistry, Vol. 29, No. 6, 08.2010, p. 289-298.

Research output: Contribution to journalArticle

Huang, Cheng Yuan ; Wang, Ning ; Fujiki, Katsumasa ; Otsuka, Yuji ; Akamatsu, Masao ; Fujimoto, Yukari ; Fukase, Koichi. / Widely applicable deprotection method of 2,2,2-trichloroethoxycarbonyl (Troc) group using tetrabutylammonium fluoride. In: Journal of Carbohydrate Chemistry. 2010 ; Vol. 29, No. 6. pp. 289-298.
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