title: Synthesis of oligosaccharides using per-O-trimethylsilyl-glycosyl iodides as glycosyl donor.
abstract: Trimethylsilyl (TMS) protecting group has been found to be very useful for the simultaneous protection of both the glycosyl donor- and the acceptor-substrates in oligosaccharide synthesis. Thus, while the per-O-trimethylsilylated glycosyl iodides served as the glycosyl donor, those bearing selectively exposed primary hydroxyl groups were found suitable as the glycosyl acceptor for the reaction. The cheap and commercially available trialkylamine, triethylamine was found to be an effective promoter for the glycosylation. Importantly, the reaction was α-stereospecific and gave the products in 58%-78% yields.
authors.affiliation: Carbohydrate Chemistry and Biotechnology, Jiangnan University Key Laboratory of Ministry of Education, Wuxi 214122, PR China.
authors.forename: Hong
authors.initials: H
authors.lastname: Wang
authors.affiliation: Department of Chemistry, Zhejiang University, Hangzhou 310027, PR China. Electronic address: cuiyl@zju.edu.cn.
authors.forename: Yanli
authors.initials: Y
authors.lastname: Cui
authors.affiliation: Department of Chemistry, Zhejiang University, Hangzhou 310027, PR China.
authors.forename: Rong
authors.initials: R
authors.lastname: Zou
authors.affiliation: Department of Chemistry, Zhejiang University, Hangzhou 310027, PR China.
authors.forename: Zhaodong
authors.initials: Z
authors.lastname: Cheng
authors.affiliation: Carbohydrate Chemistry and Biotechnology, Jiangnan University Key Laboratory of Ministry of Education, Wuxi 214122, PR China.
authors.forename: Weirong
authors.initials: W
authors.lastname: Yao
authors.affiliation: Hangzhou Yanqing Biotechnology Co., Ltd, Hangzhou 310052, PR China.
authors.forename: Yangyi
authors.initials: Y
authors.lastname: Mao
authors.affiliation: Institut Parisien de Chimie Moleculaire, UMR CNRS 8232, Universite Pierre et Marie Curie-Paris 6, 75005 Paris, France.
authors.forename: Yongmin
authors.initials: Y
authors.lastname: Zhang
mesh_terms: D006031:Glycosylation; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: D009844:Oligosaccharides; D014297:Trimethylsilyl Compounds; C419804:trimethylsilyl iodide
keywords: Glycosyl iodide; Triethylamine; Trimethylsilyl group; α-Glycosylation