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-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).
Ren
Zhong-Xu
ZX
Department of Chemistry, The University of Tennessee, Knoxville, TN 37996-1600, USA.
Yang
Qiang
Q
Price
Kenneth N
KN
Chen
Tianniu
T
Nygren
Cara
C
Turner
John F C
JF
Baker
David C
DC
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D006820:Hyaluronic Acid / Q000737:chemistry*; D007202:Indicators and Reagents; D008958:Models, Molecular; D008969:Molecular Sequence Data; D013450:Sulfones / Q000737:chemistry
D004187:Disaccharides; D007202:Indicators and Reagents; D013450:Sulfones; D006820:Hyaluronic Acid