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Cationic ring‐opening polymerization of 1,6‐anhydro‐2,3,4‐tri‐ O ‐allyl‐ β ‐ D ‐glucopyranose as a convenient synthesis of dextran
Author(s) -
Kakuchi Toyoji,
Kusuno Atsushi,
Miura Masakatsu,
Kaga Harumi
Publication year - 2000
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 - 10.1002/1521-3927(20001001)21:15<1003::aid-marc1003>3.0.co;2-n
Subject(s) - cationic polymerization , ring opening polymerization , polymerization , polymer chemistry , chemistry , polymer , yield (engineering) , propenyl , dextran , medicinal chemistry , organic chemistry , materials science , metallurgy
For the convenient synthesis of (1→6)‐ α ‐ D ‐glucopyranan, i. e., dextran ( 4 ), ring‐opening polymerization of 1,6‐anhydro‐2,3,4‐tri‐ O ‐allyl‐ β ‐ D ‐glucopyranose ( 1 ) has been carried out using BF 3 ·OEt 2 . With a ratio of [BF 3 ·OEt 2 ]/[ 1 ] = 0.5 at 0 °C for 140 h, the yield and M n of the obtained polymer are 84.0% and 21 700, respectively. The polymer consists of (1→6)‐ α ‐linked 2,3,4‐tri‐ O ‐allyl‐ D ‐glucopyranose ( 2 ) which is similar to the results for the cationic ring‐opening polymerization of 1,6‐anhydro‐2,3,4‐tri‐ O ‐methyl‐ β ‐ D ‐glucopyranose and 1,6‐anhydro‐2,3,4‐tri‐ O ‐ethyl‐ β ‐ D ‐glucopyranose. Polymer 2 was isomerized using tris(triphenylphosphine)‐chlororhodium as the catalyst in toluene/ethanol/water to yield polymeric 2,3,4‐tri‐ O ‐propenyl‐(1→6)‐ α ‐ D ‐glucopyranan ( 3 ). Deprotection of the propenyl ether linkage of 3 was then performed using hydrochloric acid in acetone to give 4 .