Ring-opening polymerization and copolymerization of a new benzylated 1,6-anhydro-3-azido-3-deoxy-beta-D-allopyranose and synthesis of amino-polysaccharides with 1,6-alpha-allopyranosidic structure

被引:12
作者
Hattori, K
Yoshida, T
Uryu, T
机构
[1] HOKKAIDO UNIV,GRAD SCH SCI,DEPT POLYMER SCI,KITA KU,SAPPORO,HOKKAIDO 060,JAPAN
[2] UNIV TOKYO,INST IND SCI,MINATO KU,TOKYO 106,JAPAN
关键词
D O I
10.1002/macp.1997.021980103
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Ring-opening polymerization of a new anhydro-hexose monomer having an azido group, 1,6-anhydro-3-azido-2,4-di-O-benzyl-3-deoxy-beta-D-allopyranose (A3ABA), was carried out with Lewis acid catalysts to give a stereoregular (1-->6)-alpha-D-allopyranan derivative having the azido group at the C3 position. The number-average molecular weights and specific rotations were 5.0 x 10(3) to 24.0 x 10(3) and +71 degrees to +79 degrees, respectively. Reduction of the azido groups into amino groups by lithium aluminium hydride and subsequent debenzylation of the benzyl groups into hydroxyl groups by sodium in liquid ammonia gave 3-amino-3-deoxy-(1-->6)-alpha-D-allopyranan in good yield. In addition, copolymerization of A3ABA with 1,6-anhydro-2,3,4-tri-O-benzyl-beta-D-glucopyranose (LGTBE) in the various feeds was carried out to afford the corresponding copolymers. The monomer reactivity ratios were calculated with the Kelen-Tudos method to be r(A3ABA) = 0.66 and r(LGTBE) = 1.67. After reduction of azido groups and deprotection of benzyl groups of the copolymers, new hetero-polysaccharides having different contents of glucopyranose and 3-amino-allopyranose units were obtained.
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页码:29 / 39
页数:11
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