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Efficient glycosylation with glycosyl ortho-allylbenzoates as donors

Author:
Liang, Haijing, Ma, Lixia, Li, Changwei, Peng, Qiang, Wang, Zhaoyan, Zhang, Zhan-xin, Yu, Lan, Liu, Huanxiang, An, Fengli, Xue, Weihua
Source:
Tetrahedron letters 2019 v.60 no.1 pp. 84-87
ISSN:
0040-4039
Subject:
biochemical pathways, chemical structure, glycosides, glycosylation, models, organic compounds
Abstract:
Glycosylation reactions are significant as they provide access to model compounds that are useful for elucidating biochemical pathways. Herein, we describe the development of glycosyl ortho-alkynylbenzoates as novel, bench-top stable, and readily available glycosyl donors. Glycosylation is promoted by inexpensive trimethylsilyl triflate (TMSOTf) in combination with N-iodosuccinimide (NIS) under mild reaction conditions; hence, the novel glycosyl donors are promising reagents for the synthesis of glycosides.
Agid:
6232205