A Stereoselective Approach for the Synthesis of α-Sialosides

A highly efficient synthesis of the human melanoma associated antigen GD3 derivative has been described. A key feature of the synthetic approach was the use of sialyl donors that were protected with a C-5 trifluoroacetamide moiety. These sialyl donors gave high yields and excellent α-anomeric select...

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Veröffentlicht in:	Journal of organic chemistry 2001-08, Vol.66 (16), p.5490-5497
Hauptverfasser:	Meo, Cristina De, Demchenko, Alexei V, Boons, Geert-Jan
Format:	Artikel
Sprache:	eng
Schlagworte:	Galactosides - chemical synthesis Galactosides - chemistry Gangliosides - chemical synthesis Gangliosides - chemistry Glycosylation Humans Molecular Conformation N-Acetylneuraminic Acid - chemistry
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creator	Meo, Cristina De Demchenko, Alexei V Boons, Geert-Jan
description	A highly efficient synthesis of the human melanoma associated antigen GD3 derivative has been described. A key feature of the synthetic approach was the use of sialyl donors that were protected with a C-5 trifluoroacetamide moiety. These sialyl donors gave high yields and excellent α-anomeric selectivities in direct glycosylations with a wide variety of glycosyl acceptors ranging from C-8 hydroxyls of sialic acids and C-3 hydroxyls of galactosides to reactive primary alcohols.
doi_str_mv	10.1021/jo010345f
format	Article
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Org. Chem</addtitle><description>A highly efficient synthesis of the human melanoma associated antigen GD3 derivative has been described. A key feature of the synthetic approach was the use of sialyl donors that were protected with a C-5 trifluoroacetamide moiety. 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subjects	Galactosides - chemical synthesis Galactosides - chemistry Gangliosides - chemical synthesis Gangliosides - chemistry Glycosylation Humans Molecular Conformation N-Acetylneuraminic Acid - chemistry
title	A Stereoselective Approach for the Synthesis of α-Sialosides
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