Synthesis of a C-linked hyaluronic acid disaccharide mimetic

Synthesis of a C-linked hyaluronic acid disaccharide mimetic

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-pyridi...

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Veröffentlicht in:Carbohydrate research 2007-09, Vol.342 (12-13), p.1668-1679
Hauptverfasser: Ren, Zhong-Xu, Yang, Qiang, Price, Kenneth N., Chen, Tianniu, Nygren, Cara, Turner, John F.C., Baker, David C.
Format: Artikel
Sprache:eng
Schlagworte:
C-Disaccharide
C-Glycosides
C-Glycosyl compounds
Carbohydrate Conformation
Carbohydrate Sequence
Disaccharides - chemical synthesis
Disaccharides - chemistry
Glycosylation
Hyaluronic Acid - chemistry
Hyaluronic acid mimetic
Indicators and Reagents
Models, Molecular
Molecular Sequence Data
Samarium diiodide
Sulfones - chemistry
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Zusammenfassung: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-β-d-glucopyranose (6), and the aldehyde, p-methoxyphenyl 2,3-di-O-benzyl-4-deoxy-4-C-formyl-6-O-p-methoxybenzyl-β-d-glucopyranoside (14).
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2007.05.031