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Synthesis of an inositol phosphoglycan fragment found in Leishmania parasites
Department of Organic Chemistry, Arrhenius Lab., Stockholm Univ., S., Stockholm, Sweden.
Linköping University, The Institute of Technology. Linköping University, Department of Physics, Chemistry and Biology.
Department of Organic Chemistry, Arrhenius Lab., Stockholm Univ., S., Stockholm, Sweden.
Department of Organic Chemistry, Arrhenius Lab., Stockholm Univ., S., Stockholm, Sweden.
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2000 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 56, no 24, 3969-3975 p.Article in journal (Refereed) Published
Abstract [en]

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.
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Engineering and Technology
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URN: urn:nbn:se:liu:diva-47636DOI: 10.1016/S0040-4020(00)00239-8OAI: oai:DiVA.org:liu-47636DiVA: diva2:268532
Available from: 2009-10-11 Created: 2009-10-11 Last updated: 2017-12-13

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Lindberg, JanKonradsson, Peter

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