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Chemical synthesis of a comb-shaped, branched stereoregular polysaccharide, 4-O-α-d-mannopyranosyl-(1 → 6)-α-d-mannopyranan

✍ Scribed by Kazukiyo Kobayashi; Koji Nomura; Masahiko Okada

Publisher
Elsevier Science
Year
1993
Tongue
English
Weight
473 KB
Volume
242
Category
Article
ISSN
0008-6215

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✦ Synopsis

4-O-alpha-D-Mannopyranosyl-(1-->6)-alpha-D-mannopyranan (7) was prepared via ring-opening polymerization of 1,6-anhydro-2,3-di-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-alpha-D- mannopyranosyl)-beta-D-mannopyranose (5) using phosphorus pentafluoride as initiator in dichloromethane at -60 degrees C, followed by debenzylation. Compound 5 was obtained via glycosidation of 1,6-anhydro-2,3-O- isopropylidene-beta-D-mannopyranose (1) with 2,3,4,6-tetra-O-benzyl-1-O-trichloroacetimidoyl-alpha-D-mannopyran ose (2) using p-toluenesulfonic acid as catalyst and subsequent transformation of the protecting groups of the resulting 1,6-anhydro-4-O-(2,3,4,6-tetra-O-benzyl-alpha-D-mannopyranosyl)-2,3- O-isopropylidene-beta-D-mannopyranose (3).

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