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Synthesis of a C-linked hyaluronic acid disaccharide mimetic.

ABSTRACT: The synthesis of a C-disaccharide that is designed as a mimetic for the repeating unit disaccharide of hyaluronic acid is described. The target compound was obtained via the SmI2-promoted coupling reaction of the sulfone, 2-acetamido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1,2-dideoxy-1-pyridinylsulfonyl-beta-D-glucopyranose (6), and the aldehyde, p-methoxyphenyl 2,3-di-O-benzyl-4-deoxy-4-C-formyl-6-O-p-methoxybenzyl-beta-D-glucopyranoside (14).

SUBMITTER: Ren ZX

PROVIDER: S-EPMC1989762 | biostudies-literature | 2007 Sep

REPOSITORIES: biostudies-literature

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Synthesis of a C-linked hyaluronic acid disaccharide mimetic.

Ren Zhong-Xu ZX Yang Qiang Q Price Kenneth N KN Chen Tianniu T Nygren Cara C Turner John F C JF Baker David C DC

Carbohydrate research 20070602 12-13

The synthesis of a C-disaccharide that is designed as a mimetic for the repeating unit disaccharide of hyaluronic acid is described. The target compound was obtained via the SmI2-promoted coupling reaction of the sulfone, 2-acetamido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1,2-dideoxy-1-pyridinylsulfonyl-beta-D-glucopyranose (6), and the aldehyde, p-methoxyphenyl 2,3-di-O-benzyl-4-deoxy-4-C-formyl-6-O-p-methoxybenzyl-beta-D-glucopyranoside (14). ...[more]

PMID: 17572398

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