146934-39-6

Basic information

• Product Name: 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl chloride
• Synonyms: 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl chloride
• CAS NO: 146934-39-6
• Molecular Weight: 467.303
• Mol File: 146934-39-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl chloride(146934-39-6)
• EPA Substance Registry System: 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl chloride(146934-39-6)

Safety Data

• Hazardous Substances Data: 146934-39-6(Hazardous Substances Data)

Upstream product

• 151072-05-8 2-(trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranoside 
• 145836-01-7 Methyl 2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside 
• 151072-02-5 2-(trimethylsilyl)ethyl 2,3-O-isopropylidene-α-L-rhamnopyranoside 
• 146934-37-4 2-(Trimethylsilyl)ethyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside 
• 146934-36-3 2-(Trimethylsilyl)ethyl α-L-rhamnopyranoside 
• 218279-58-4 methyl 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranoside 
• 88331-96-8 methyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside 
• 115678-08-5 methyl 1-thio-α-L-rhamnopyranoside 
• 98-88-4 benzoyl chloride 
• 707-07-3 orthobenzoic acid trimethyl ester 
• 151072-03-6 2-(trimethylsilyl)ethyl 4-O-benzoyl-2,3-O-isopropylidene-α-L-rhamnopyranoside 
• 151072-04-7 2-(trimethylsilyl)ethyl 4-O-benzoyl-α-L-rhamnopyranoside 
• 146934-38-5 Methyl 2,4-di-O-benzoyl-3-O-chloroacetyl-1-thio-α-L-rhamnopyranoside 

Downstream Products

• 146934-41-0 1-(Trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside 
• 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 
• 218279-78-8 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-α-D-xylo-hexopyranoside 
• 218279-72-2 methyl (2,4-di-O-benzoyl-3-O-chloroacetyl-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 
• 218279-77-7 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-α-D-xylo-hexopyranoside 
• 218279-76-6 methyl (3,4,6-tri-O-acetyl-2-amino-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-α-D-xylo-hexopyranoside 
• 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 
• 146934-40-9 1-(Trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-(2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside 

Relevant articles and documents

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.

Synthesis of tetrasaccharide building block of the O-specific polysaccharide of Shigella dysenteriae type 1

A glycosyl trichloroacetimidate derivative (1) of the tetrasaccharide α-D-Galp-(1→3)-α-D-GlcpNAc-(1→3)-α-L-Rhap-(1→3)-α-L-Rhap was synthesized in a highly stereoselective, stepwise manner, using methyl 1-thioglycosides of L-rhamnose, 2-azido-2-deoxy-D-glucose and D-galactose, as major intermediates. The protecting group scenario in compound 1 permits regioselective deblocking at its 'non-reducing end' unit. Therefore 1 is a suitable intermediate for the preparation of extended fragments of the title polysaccharide.