A new glycosylation method part 3: study of microwave effects at low temperatures to control reaction pathways and reduce byproducts |
| |
Authors: | Hiroki Shimizu Yayoi Yoshimura Shin-Ichiro Nishimura |
| |
Affiliation: | a Drug-Seeds Discovery Research Laboratory, Hokkaido Center, National Institute of Advanced Industrial Science and Technology (AIST), Sapporo 062-8517, Japan b Division of Advanced Chemical Biology, Graduate School of Advanced Life Science, Frontier Research Center for Post-Genomic Science and Technology, Hokkaido University, Sapporo 011-0021, Japan |
| |
Abstract: | The efficiency of microwave irradiation at low temperature for glycosylations is described. Although oligosaccharide synthesis usually requires reactive donors for glycosylations, which have leaving groups on the anomer positions, i.e., trichloroacetoimidates, halogenates, thioalkyl glycosides, etc., the suitable donors in our microwave supported synthesis of Lewis X oligosaccharide were very stable acetate derivatives. Regarding glycosylation with a fucosyl acetate donor and a glucosamine acceptor, microwave irradiation with simultaneous cooling improved yields. Moreover, further synthesis to Lewis X derivatives was achieved only with microwave irradiation at low temperatures. Without microwave irradiation, we could only obtain byproducts and none of the designed product at any reaction temperature. |
| |
Keywords: | Microwave Nonthermal effect Glycosylation Carbohydrate |
本文献已被 ScienceDirect 等数据库收录! |
|