Synthesis of an Inositol Phosphoglycan Fragment found in Leishmania Parasites

Synthesis of 1 and 2a is described using a block synthetic strategy. Compound 4 was used as precursor for the two mannose derivatives which, coupled together, forms the dimannoside building block. Thioglycoside 7 was coupled to 8 yielding inositol phosphoglycan 9a, which was selectively deprotected...

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Bibliographic Details
Published in:Tetrahedron 2000-06, Vol.56 (24), p.3969-3975
Main Authors: Ruda, Katinka, Lindberg, Jan, Garegg, Per J, Oscarson, Stefan, Konradsson, Peter
Format: Article
Language:English
Subjects:
inositol phosphoglycan
Leishmania parasites
oligosaccharides
TECHNOLOGY
TEKNIKVETENSKAP
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Summary:Synthesis of 1 and 2a is described using a block synthetic strategy. Compound 4 was used as precursor for the two mannose derivatives which, coupled together, forms the dimannoside building block. Thioglycoside 7 was coupled to 8 yielding inositol phosphoglycan 9a, which was selectively deprotected and reacted with 2,3,4,6-tetra- O-benzyl-α- d-glucopyranos-1-yl H-phosphonate to form the protected target molecule 12. Deprotection of 12 by acidic deacetalisation/desilylation and subsequent catalytic hydrogenolysis resulted in cleavage of the anomeric phosphodiester to produce 1. Debenzylation with sodium in liquid ammonia followed by acidic deacetalisation/desilylation gave the target compound 2a.
ISSN:0040-4020
1464-5416
1464-5416
DOI:10.1016/S0040-4020(00)00239-8