L-iduronic acid derivatives as glycosyl donors.
O-[Methyl (2-O-acetyl-3-O-benzyl-4-O-levulinyl-alpha, and beta-L-idopyranosid)uronate] trichloroacetimidate and the corresponding n-pentenyl glycosides are efficient L-iduronic acid glycosyl donors. Both have been used for the high-yielding synthesis of basic disaccharide blocks which are useful for the subsequent synthesis of complex oligosaccharides related to heparin/heparan sulfate, and dermatan sulfate. In contrast, the corresponding thioethyl glycosides, thiophenyl glycosides, and fluoride, did not yield the expected disaccharides.
Tabeur
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C
Département de Chimie, URA CNRS 1686, Paris, France.
Machetto
F
F
Mallet
J M
JM
Duchaussoy
P
P
Petitou
M
M
Sinaÿ
P
P
D002240:Carbohydrate Sequence; D005459:Fluorides / Q000737:chemistry; D006031:Glycosylation; D007067:Iduronic Acid / Q000031:analogs & derivatives* / Q000737:chemistry; D008969:Molecular Sequence Data
D007067:Iduronic Acid; D005459:Fluorides