218279-72-2

Upstream product

• 218279-59-5 methyl (2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-(1-3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside 
• 218279-58-4 methyl 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranoside 
• 146934-39-6 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl chloride 
• 88331-96-8 methyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside 
• 218279-60-8 (2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranosyl chloride 

Downstream Products

• 218279-82-4 methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-3-deoxy-3-fluoro-α-D-galactopyranoside 
• 218279-80-2 methyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-4,6-O-benzylidene-3-deoxy-3-fluoro-α-D-galactopyranoside 
• 218279-81-3 methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-4,6-O-benzylidene-3-deoxy-3-fluoro-α-D-galactopyranoside 
• 218279-74-4 methyl (2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-4,6-O-benzylidene-3-deoxy-3-fluoro-α-D-galactopyranoside 

Relevant academic research and scientific papers

Synthesis of tri- and tetrasaccharide fragments of the Shigella dysenteriae type 1 O-antigen deoxygenated and fluorinated at position 3 of the methyl α-D-galactopyranoside terminus

The blockwise synthesis of methyl alpha tri- and tetrasaccharide analogs of the biochemical repeating unit of the Shigella dysenteriae type 1 O-polysaccharide is described. Modifications include deoxygenation and deoxyfluorination at position 3 of the galactopyranoside residue. Methyl 4,6-O-benzylidene-3-deoxy-α-D-xylo-hexopyranoside (8) and methyl 4,6-O-benzylidene-3-deoxy-3-fluoro-α-D-galactopyranoside (9) were condensed with (2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1→3)-2,4-di-O-benzoyl-α-L-rhamnopyranosyl chloride to give, after deprotection, the target trisaccharide methyl α-L-rhamnopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-3-deoxy-α-D-xylo-hexopyranoside and the corresponding fluorinated oligosaccharide. For the tetrasaccharide synthesis, the glycosyl acceptors 8 and 9 were condensed with the temporarily protected (2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-(1→3)-2,4-di-O-benzoyl-α-L-rhamnopyranosyl chloride. Removal of the chloroacetyl group was followed by condensation of the resulting selectively deblocked trisaccharides with 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl chloride. Reduction and deprotection then gave the free methyl 2-acetamido-2-deoxy-α-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-3-deoxy-α-D-xylo-hexopyranoside and the fluorinated analog. Copyright (C) 1998 Elsevier Science Ltd.