294623-63-5

Upstream product

• 100-46-9 benzylamine 
• 294623-62-4 methyl 4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-altropyranoside 
• 5328-47-2 (4aR,6S,7S,8S,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 33164-03-3 methyl 2,3-di-O-benzyl-α-D-altropyranoside 
• 100-44-7 benzyl chloride 
• 99212-27-8 methyl 4,6-O-benzylidene-2,3-di-O-benzyl-α-D-altropyranoside 
• 118068-39-6 methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-altropyranoside 

Downstream Products

• 294623-64-6 (2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine 
• 294623-65-7 4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine 
• 294623-69-1 4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl-3-O-(β-D-galactopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-2-ethyl-3,4-dihydroxypyrrolidine 
• 294623-68-0 4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-2-ethyl-3,4-dihydroxypyrrolidine 

Relevant academic research and scientific papers

Synthesis of a novel sialyl lewis X analogue containing a pyrrolidine in place of N-acetyl glucosamine 1

The synthesis of the new sialyl Lewis X analogue, 4-O-(α-L-fucopyranosyl)-3-O-(3-O-sodium sulfonato-β-D-galactopyranosyl)-(2S,3R, 4R)-2-ethyl-3,4-dihydroxypyrrolidine 2 has been achieved. The N-acetyl glucosamine unit of natural Lewis X has been replaced by a rigid 3R/4R-dihydroxylated pyrrolidine 12. This one has been synthezised from the methyl 4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-altropyranoside sugar precursor 10 using the Ganem/Bemotas one-pot elimination-reductive amination ring contraction reaction. The (2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine 12 obtained was subsequently regioselectively glycosylated, using 2,3,4-tri-O-benzyl-α-L-fucopyranosyl fluoride and 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl bromide as glycosyl donors. Disaccharide containing pyrrolidine 21 was finally transformed into the target O-sulfated analog 2, after regioselective sulfation and usual deprotection.