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

✍ Scribed by Kazuyuki Hattori; Takashi Yoshida; Toshiyuki Uryu

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
548 KB
Volume
198
Category
Article
ISSN
1022-1352

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✦ Synopsis

Abstract

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‐β‐D‐allopyranose (A3ABA), was carried out with Lewis acid catalysts to give a stereoregular (1→6)‐α‐D‐allopyranan derivative having the azido group at the C3 position. The number‐average molecular weights and specific rotations were 5.0 × 10^3^ to 24.0 × 10^3^ and +71° to +79°, respectively. Reduction of the azido groups into amino groups by lithium aluminium hydride and subsequent debenzylation of the benzyl group into hydroxyl groups by sodium in liquid ammonia gave 3‐amino‐3‐deoxy‐(1→6)‐α‐D‐allopyranan in good yield. In addition, copolymerization of A3ABA with 1,6‐anhydro‐2,3,4‐tri‐O‐benzyl‐β‐D‐glucopyranose (LGTBE) in the various feeds was carried out to afford the corresponding copolymers. The monomer reactivity ratios were calculated with the Kelen‐Tüdős 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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