Widely Applicable Deprotection Method of 2,2,2-Trichloroethoxycarbonyl (Troc) Group Using Tetrabutylammonium Fluoride

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 se...

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Published inJournal of carbohydrate chemistry Vol. 29; no. 6; pp. 289 - 298
Main Authors Huang, Cheng-yuan, Wang, Ning, Fujiki, Katsumasa, Otsuka, Yuji, Akamatsu, Masao, Fujimoto, Yukari, Fukase, Koichi
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis Group 01.08.2010
Taylor & Francis
Taylor & Francis Ltd
Subjects
2,2,2-Trichloroethoxycarbonyl group
Biochemistry & Molecular Biology
Chemistry
Chemistry, Organic
Deprotection
Fluorides
Glucosamine
Life Sciences & Biomedicine
Physical Sciences
Science & Technology
Tetrabutylammonium fluoride
MILD
Tetrabutylammonium fluoride
2
Glucosamine
2-Trichloroethoxycarbonyl group
Deprotection
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Summary: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.
Bibliography:ObjectType-Article-2
SourceType-Scholarly Journals-1
ObjectType-Feature-1
content type line 23
ISSN:0732-8303
1532-2327
DOI:10.1080/07328303.2010.512405