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C-5 Modified S-Benzoxazolyl Sialyl Donors: Towards More Efficient Selective Sialylations

✍ Scribed by Benjamin N. Harris; Payal P. Patel; Chase P. Gobble; Matthew J. Stark; Cristina De Meo

Publisher: John Wiley and Sons
Year: 2011
Tongue: English
Weight: 389 KB
Volume: 2011
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.201100539

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✦ Synopsis

We previously reported that the selective activation of an Sbenzoxazolyl (SBox) sialyl donor over a galactosyl acceptor equipped with a thioethyl anomeric moiety can be performed in high yield but with poor stereoselectivity. To optimize this strategy, which allows the synthesis of complex carbohydrates to be shortened, a range of SBox sialyl donors modi-Scheme 1. (a) Selective activation for the synthesis of sialosides; (b) 4,5-oxazolidinone-directed α-sialylation.