Synthesis of an Inositol Phosphoglycan Fragment found in Leishmania Parasites

Autor:	Jan Lindberg, Per J. Garegg, Katinka Ruda, Peter Konradsson, Stefan Oscarson
Rok vydání:	2000
Předmět:	Anomer Stereochemistry Organic Chemistry Mannose Cleavage (embryo) Biochemistry Catalysis chemistry.chemical_compound chemistry Hydrogenolysis Drug Discovery Phosphodiester bond Molecule Inositol
Zdroj:	Tetrahedron. 56:3969-3975
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(00)00239-8
Popis:	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 .
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::5788065ee3901a0e0237542ba446915e https://doi.org/10.1016/s0040-4020(00)00239-8 Zobrazit plný text záznamu Full Text from ScienceDirect