TY - JOUR
T1 - Widely applicable deprotection method of 2,2,2-trichloroethoxycarbonyl (Troc) group using tetrabutylammonium fluoride
AU - Huang, Cheng Yuan
AU - Wang, Ning
AU - Fujiki, Katsumasa
AU - Otsuka, Yuji
AU - Akamatsu, Masao
AU - Fujimoto, Yukari
AU - Fukase, Koichi
N1 - Funding Information:
This work was supported in part by Grants in Aid for Scientific Research (No. 19310144) from the Japan Society for the Promotion of Science, as well as a grant from the Osaka University G-COE program “Global Education and Research Center for Bio-Environmental Chemistry” (to CH).
PY - 2010/8
Y1 - 2010/8
N2 - 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.
AB - 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.
KW - 2,2,2-Trichloroethoxycarbonyl group
KW - Deprotection
KW - Glucosamine
KW - Tetrabutylammonium fluoride
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U2 - 10.1080/07328303.2010.512405
DO - 10.1080/07328303.2010.512405
M3 - Article
AN - SCOPUS:77957839656
SN - 0732-8303
VL - 29
SP - 289
EP - 298
JO - Journal of Carbohydrate Chemistry
JF - Journal of Carbohydrate Chemistry
IS - 6
ER -