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Regio‐ and stereoselective cyclopolymerization of 1,2 : 4,5‐dianhydro‐3‐ O ‐methyl‐xylitol leading to a novel polycarbohydrate of (2→5)‐1,4‐anhydro‐3‐ O ‐methyl‐pentitol
Author(s) -
Satoh Toshifumi,
Shibata Ken,
Yokota Kazuaki,
Kakuchi Toyoji
Publication year - 1999
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/(sici)1521-3927(19990201)20:2<55::aid-marc55>3.0.co;2-z
Subject(s) - cationic polymerization , stereoselectivity , polymer , xylitol , chemistry , polymer chemistry , yield (engineering) , anomer , polymerization , stereochemistry , organic chemistry , catalysis , materials science , fermentation , metallurgy
(2→5)‐1,4‐Anhydro‐3‐ O ‐methyl‐pentitol, which is a novel carbohydrate polymer without an anomeric linkage, was synthesized by cationic cyclopolymerization of 1,2 : 4,5‐dianhydro‐3‐ O ‐methyl‐xylitol. When BF 3 ·OEt 2 was used as the initiator, soluble polymers were obtained in 28 to 50% yield. These polymers have number‐average molecular weights of 1 150 to 2 340 corresponding to an average degree of polymerization of 8.8 to 18.0. It was confirmed by 13 C NMR that the resulting polymer mainly consists of 1,4‐anhydro‐3‐ O ‐methyl‐ D L ‐arabinitol units.