Synthesis of an inositol phosphoglycan fragment found in Leishmania parasites
2000 (English)In: Tetrahedron, ISSN 0040-4020, Vol. 56, no 24, 3969-3975 p.Article in journal (Refereed) Published
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-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. (C) 2000 Published by Elsevier Science Ltd.
Place, publisher, year, edition, pages
2000. Vol. 56, no 24, 3969-3975 p.
Engineering and Technology
IdentifiersURN: urn:nbn:se:liu:diva-47636DOI: 10.1016/S0040-4020(00)00239-8OAI: oai:DiVA.org:liu-47636DiVA: diva2:268532