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Synthesis of 3-amino-ribofuranans having 1,5-α and -β structures by selective ring-opening polymerization of a 1,4-anhydro-3-azido-3-deoxy-α-D-ribopyranose derivative

✍ Scribed by Byoung Won Kang; Kazuyuki Hattori; Takashi Yoshida; Makoto Hirai; Yoon Soung Chio; Toshiyuki Uryu

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

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✦ Synopsis

Abstract

Ring‐opening polymerization of a new anhydro ribose‐type monomer, 1,4‐anhydro‐3‐azido‐3‐deoxy‐2‐O‐tert‐butyldimethylsilyl‐α‐D‐ribopyranose (A3ASR), was investigated. The monomer was synthesized from 1,4‐anhyro‐α‐D‐xylopyranose by three steps comprising Walden inversion at the C3 position into ribose configuration. Ring‐opening polymerization of A3ASR by Lewis acid catalysts such as boron trifluoride etherate and stannic chloride gave a stereoregular 3‐azido‐3‐deoxy‐2‐O‐tert‐butyldimethylsilyl‐(1→5)‐α‐D‐ribofuranan having specific rotations of +246 ∼ +271 deg · dm^−1^ · g^−1^ · cm^3^ and number‐average molecular weights of 18,7 × 10^3^ ∼ 25,1 × 10^3^. When the polymerization was carried out by antimony pentachloride at 0°C, the resulting polymer exhibited a negative specific rotation of −6 deg · dm^−1^ · g^−1^ · cm^3^ and the C1 absorption in the ^13^C NMR spectrum shifted downfield to 107,5 ppm, suggesting that the polymer might consist of 1,5‐β furanosidic unit. The reduction of the azido group of the 1,5‐α and 1,5‐β furanosidic polymers into amino group and subsequent desilylation gave 3‐amino‐3‐deoxy‐(1→5)‐α‐ and ‐β‐D‐ribofuranans, respectively. In addition, copolymerization of A3ASR with 1,4‐anhydro‐2,3‐di‐O‐tert‐butyldimethylsilyl‐α‐D‐ribopyranose (ADSR) in various feeds was performed by boron trifluoride etherate as catalyst to give copolymers with different monomeric components. The structural analysis of the homopolymers and copolymers was examined by means of ^1^H and ^13^C NMR spectroscopies, IR spectroscopy, and optical rotation.

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