289057-13-2

Upstream product

• 289057-09-6 ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside 
• 289057-10-9 ethyl 2,4-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside 
• 153185-20-7 ethyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside 
• 100-39-0 benzyl bromide 
• 289057-11-0 ethyl 2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranoside 

Downstream Products

• 289057-14-3 ethyl (2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 

Relevant academic research and scientific papers

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 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. (C) 2000 Published by Elsevier Science Ltd.