The Utility of a 3-O-Allyl Group as a Protective Group for Ring-Opening Polymerization of α-d-Glucopyranose 1,2,4-Orthopivalate Derivatives
- 25 April 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Biomacromolecules
- Vol. 3 (3) , 538-546
- https://doi.org/10.1021/bm015656e
Abstract
To clarify the utility as a protective group of 3-O-allyl group on ring-opening polymerization of alpha-D-glucopyranose 1,2,4-orthopivalate derivatives, four orthopivalate derivatives, 3-O-allyl-6-O-pivaloyl- (1), 3-O-allyl-6-O-benzyl- (2), 3,6-di-O-allyl- (3), and 3-O-allyl-6-O-methyl-alpha-D-glucopyranose 1,2,4-orthopivalates (4), were selected as starting monomers and were polymerized under -30 degrees C in CH2Cl2 using BF3.Et2O as a catalyst. All the orthopivalate derivatives 1-4 were found to give stereoregular polysaccharides, (1-->4)-beta-D-glucopyranans. Thus, it was concluded that the allyl group as a protective group at 3-O position of glucose othropivalate is acceptable to yield stereoregular (1-->4)-beta-D-glucopyranans, cellulose derivatives.Keywords
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