289057-10-9

Upstream product

• 100-39-0 benzyl bromide 
• 7473-36-1 ethyl 1-thio-α-D-mannopyranoside 
• 142924-31-0 S-ethyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 32934-24-0 S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 153185-20-7 ethyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside 
• 289057-09-6 ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside 

Relevant academic research and scientific papers

A versatile approach to the synthesis of glycans containing mannuronic acid residues

Reported herein is a new method for a highly effective synthesis of β-glycosides from mannuronic acid donors equipped with the 3-O-picoloyl group. The stereocontrol of glycosylations was achieved by means of the H-bond-mediated aglycone delivery (HAD). The method was utilized for the synthesis of a tetrasaccharide linkedviaβ-(1 → 3)-mannuronic linkages. We have also investigated 3,6-lactonized glycosyl donors that provided moderate to high β-manno stereoselectivity in glycosylations. A method to achieve complete α-manno stereoselectivity with mannuronic acid donors equipped with 3-O-benzoyl group is also reported.

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.