l-Iduronic acid derivatives as glycosyl donors

O-[Methyl (2- O-acetyl-3- O-benzyl-4- O-levulinyl- α, and β 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 th...

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Bibliographic Details
Published in:Carbohydrate research 1996-02, Vol.281 (2), p.253-276
Main Authors: Tabeur, Christine, Machetto, Françoise, Mallet, Jean-Maurice, Duchaussoy, Philippe, Petitou, Maurice, Sinaÿ, Pierre
Format: Article
Language:English
Subjects:
Carbohydrate Sequence
Fluorides - chemistry
Glycosaminoglycans
Glycosidation
Glycosyl donors
Glycosylation
Iduronic acid
Iduronic Acid - analogs & derivatives
Iduronic Acid - chemistry
Molecular Sequence Data
Synthesis
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Summary:O-[Methyl (2- O-acetyl-3- O-benzyl-4- O-levulinyl- α, and β 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.
ISSN:0008-6215
1873-426X
DOI:10.1016/0008-6215(95)00346-0