NDLI: The α-Glycosidation of Partially Unprotected N-Acetyl and N-Glycolyl Sialyl Donors in the Absence of a Nitrile Solvent Effect

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The α-Glycosidation of Partially Unprotected N-Acetyl and N-Glycolyl Sialyl Donors in the Absence of a Nitrile Solvent Effect

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Uzawa, Jun Yamaguchi, Yoshiki Aoyagi, Taku Ohira, Shuichi Tanaka, Hiroshi Fuse, Shinichiro
Description	Author Affiliation: Aoyagi T ( Department of Chemical Science and Engineering, Tokyo Institute of Technology, 2-12-1-H101 Ookayama, Meguro, Tokyo, 152-8552, Japan.); Ohira S ( Department of Chemical Science and Engineering, Tokyo Institute of Technology, 2-12-1-H101 Ookayama, Meguro, Tokyo, 152-8552, Japan.); Fuse S ( Department of Chemical Science and Engineering, Tokyo Institute of Technology, 2-12-1-H101 Ookayama, Meguro, Tokyo, 152-8552, Japan.); Uzawa J ( Laboratory of Chemical and Life Science, Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama, 226-8503, Japan.); Yamaguchi Y ( RIKEN-Max-Planck Joint Research Center for Systems Chemical Biology, RIKEN Global Research Cluster, 2-1 Hirosawa, Wako, 351-0198, Saitama, Japan.); Tanaka H ( RIKEN-Max-Planck Joint Research Center for Systems Chemical Biology, RIKEN Global Research Cluster, 2-1 Hirosawa, Wako, 351-0198, Saitama, Japan.)
Abstract	The synthesis of α-sialosides is one of the most difficult reactions in carbohydrate chemistry and is considered to be both a thermodynamically and kinetically disfavored process. The use of acetonitrile as a solvent is an effective solution for the α-selective glycosidation of N-acetyl sialic acids. In this report, we report on the α-glycosidation of partially unprotected N-acetyl and N-glycolyl donors in the absence of a nitrile solvent effect. The 9-O-benzyl-N-acetylthiosialoside underwent glycosidation in $CH_{2}Cl_{2}$ with a good α-selectivity. On the other hand, the 4,7,8-O-triacetyl-9-O-benzyl-N-acetylthiosialoside was converted to β-sialoside as a major product under the same reaction conditions. The results indicate that the O-acetyl protection of the sialyl donor was a major factor in reducing the α-selectivity of sialylation. After tuning of the protecting groups of the hydroxy groups at the 4,7,8 position on the sialyl donor, we found that the 9-O-benzyl-4-O-chloroacetyl-N-acetylthiosialoside underwent sialylation with excellent α-selectivity in $CH_{2}Cl_{2}.$ To demonstrate the utility of the method, straightforward synthesis of α(2,9) disialosides containing N-acetyl and/or N-glycolyl groups was achieved by using the two N-acetyl and N-glycolyl sialyl donors.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	20
Volume Number	22
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2016-05-10
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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