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Regioselectivity shift from β-(1→6)- to β-(1→3)-glycosylation of non-protected methyl β-d-galactopyranosides using the stannylene activation method

✍ Scribed by Eisuke Kaji; Keigo Shibayama; Kazusada In

Book ID
104253790
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
153 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

Regio-and stereoselective glycosylation of non-protected methyl b-D-galactopyranoside has been developed using the stannylene acetal mediator, allowing a one-pot assembly of glucosyl-b-( 16)-galactose and glucosyl-b-(13)-galactose. Remarkable regioselectivity shift from b-( 16)to b-(13)-glycosylation has been observed by addition of Bu 4 NF etc. to the reaction medium. The method requires no tedious, lengthy manipulation being employed for the conventional protection-deprotection method.

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