174089-83-9

Upstream product

• 14218-11-2 2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide 
• 174089-82-8 methyl 3-O-benzyl-2-deoxy-2-iodo-6-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 174089-81-7 methyl 3-O-benzyl-2-deoxy-2-iodo-α-D-glucopyranoside 
• 2774-19-8 (2R,4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 

Downstream Products

• 174089-85-1 methyl 4-O-acetyl-2-deoxy-6-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-3-O-(2,4,6-tri-O-acetyl-3-deoxy-α-D-arabino-hexopyranosyl)-α-D-arabino-hexopyranoside 

Relevant academic research and scientific papers

Syntheses of deoxy analogues of methyl 3,6-di-O-α-D-mannopyranosyl-α-D-mannopyranoside for studies of the binding site of concanavalin A

All of the monodeoxy analogues of methyl 3,6-di-O-α-D-mannopyranosyl-α-D-mannopyranoside have been synthesized together with two dideoxy (2,3'- and 4,3'-) analogues. The 2'- and 2''-deoxy functions were introduced by NIS-promoted couplings with 2,3,4-tri-O-acetyl-D-glucal as donor, followed by reduction of the resulting 2'- and 2''-iodo derivatives, whereas the 3'-, 3''-, 4'-, 4''-, 6'-, and 6''-deoxy functions were introduced by using known deoxyglycosyl chlorides as donors in coupling reactions promoted by silver trifluoromethanesulfonate. The 2- and 4-deoxy functions on the central mannose residue were introduced by displacement, using triiodoimidazole and triphenylphosphine, of a hydroxyl group by iodine on suitably protected derivatives followed by reduction of the resulting iodo analogues.