Synthesis of Oligosaccharides of Motifs D and E of Arabinogalactan Present in Mycobacterium tuberculosis

Syntheses of the ethyl glycosides of 5-O-(beta-D-galactofuranosyl)-beta-D-galactofuranose and 5-O-(alpha-D-arabinofuranosyl)-6-O-(beta-D-galactofuranosyl)-beta-D-galactofuranose present in motifs D and E of Mycobacterium tuberculosis arabinogalactan, respectively, have been presented. The pentenyl-m...

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Bibliographic Details
Published in:Journal of organic chemistry 2001-06, Vol.66 (13), p.4657-4660
Main Authors: GURJAR, Mukund K., REDDY, L. Krishnakanth, HOTHA, Srinivas
Format: Article
Language:English
Subjects:
Carbohydrate Sequence
Galactans - chemical synthesis
Galactans - chemistry
Molecular Conformation
Mycobacterium tuberculosis - chemistry
Oligosaccharides - chemical synthesis
Oligosaccharides - chemistry
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Summary:Syntheses of the ethyl glycosides of 5-O-(beta-D-galactofuranosyl)-beta-D-galactofuranose and 5-O-(alpha-D-arabinofuranosyl)-6-O-(beta-D-galactofuranosyl)-beta-D-galactofuranose present in motifs D and E of Mycobacterium tuberculosis arabinogalactan, respectively, have been presented. The pentenyl-mediated O-glycosylation reaction was utilized to obtain the disaccharide of motif D. The first coupling reaction to prepare the inner disaccharide portion of motif E was accomplished by trichloroacetamidate method while the installation of the terminal sugar by pentenyl glycosylation approach was successful.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo010180a