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Regioselective end-functionalization of polylactide oligomers with D-glucose and D-galactose

✍ Scribed by Katty Bernard; Philippe Degée; Philippe Dubois

Book ID
104526600
Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
120 KB
Volume
52
Category
Article
ISSN
0959-8103

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✦ Synopsis

Abstract

D‐glucose and D‐galactose end‐functionalized polylactide oligomers were synthesized by controlled ring‐opening polymerization of lactide using aluminium triisopropoxide, triethylaluminium or stannous octoate as promoter. Accordingly, two selectively protected monosaccharides were studied as co‐initiators, either 1,2;5,6‐di‐O‐isopropylidene‐α‐D‐glucofuranose (1) and 1,2;3,4‐di‐O‐isopropylidene‐α‐D‐galactopyranose (2). In contrast to what is known in polymerization of ϵ‐caprolactone, both protected monosaccharides proved to be efficient co‐initiators and yielded end‐functionalized polylactide chains with controlled regioselectivity (C‐3 or C‐6 linkage), predictable molecular weights and narrow molecular weight distributions.

© 2003 Society of Chemical Industry

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## Abstract Sugar–iminosugar hybrid molecules made up of D‐glucose and D‐galactose with pyrrolidine‐based iminosugars, viz. 1,4‐dideoxy‐1,4‐imino‐L‐xylitol and 1,4‐dideoxy‐1,4‐imino‐L‐lyxitol, are synthesized from glycal epoxides and found to be moderate glycosidase inhibitors. (© Wiley‐VCH Verlag