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Practical synthesis of latent disarmed S-2-(2-propylthio)benzyl glycosides for interrupted Pummerer reaction mediated glycosylation
Authors:Yang Xu  Qian Zhang  Ying Xiao  Pinru Wu  Wei Chen  Zejin Song  Xiong Xiao  Lingkui Meng  Jing Zeng  Qian Wan
Affiliation:1. Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Huazhong University of Science and Technology, 13 Hangkong Road, Wuhan, Hubei 430030, China;2. Institute of Brain Research, Huazhong University of Science and Technology, 13 Hangkong Road, Wuhan, Hubei 430030, China
Abstract:
Practical synthetic methods to latent disarmed S-2-(2-propylthio)benzyl (SPTB) glycosides for interrupted Pummerer reaction mediated glycosylation have been discovered. Among them, both coupling reaction of PTB-Cl with glycosyl thiols and BF3·OEt2 promoted reaction of peracylated glycosides with PTB-SH produced peracylated SPTB glycosides in large scales and with high efficiency.
Keywords:Interrupted Pummerer reaction  Thioglycoside  Disarmed glycoside  Glycosyl donor
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