Synthesis of an Inositol Phosphoglycan Fragment found in Leishmania Parasites

✍ Scribed by Katinka Ruda; Jan Lindberg; Per J Garegg; Stefan Oscarson; Peter Konradsson

• Book ID: 104202655
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 145 KB
• Volume: 56
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(00)00239-8

✦ Synopsis

AbstractÐSynthesis 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-a-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.