148164-03-8

Basic information

• Product Name: 1,5-anhydro-3-O-benzoyl-4-O-benzyl-2,6-dideoxy-L-arabino-hex-1-enitol
• Synonyms: 1,5-anhydro-3-O-benzoyl-4-O-benzyl-2,6-dideoxy-L-arabino-hex-1-enitol
• CAS NO: 148164-03-8
• Molecular Weight: 324.376
• Mol File: 148164-03-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1,5-anhydro-3-O-benzoyl-4-O-benzyl-2,6-dideoxy-L-arabino-hex-1-enitol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-anhydro-3-O-benzoyl-4-O-benzyl-2,6-dideoxy-L-arabino-hex-1-enitol(148164-03-8)
• EPA Substance Registry System: 1,5-anhydro-3-O-benzoyl-4-O-benzyl-2,6-dideoxy-L-arabino-hex-1-enitol(148164-03-8)

Safety Data

• Hazardous Substances Data: 148164-03-8(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 104006-65-7 1,5-anhydro-3-O-benzoyl-2,6-dideoxy-L-arabino-hex-1-enitol 
• 53657-42-4 L-rhamnal 
• 34819-86-8 3,4-di-O-acetyl-6-deoxy-L-glucal 
• 5158-64-5 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide 

Downstream Products

• 864815-52-1 methyl (2,3,4-tri-O-benzyl-α-L-mannopyranosyl)-(1->3)-(4-O-benzyl-2-chloro-2-deoxy-α-L-rhamnopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-(N-fluorenylmethoxycarbonyl-β-alanyl)-amido-β-D-glucopyranoside 
• 864815-51-0 methyl (2,3,4-tri-O-benzyl-6-O-tert-butyldimethylsilyl-α-L-mannopyranosyl)-(1->3)(4-O-benzyl-2-chloro-2-deoxy-α-L-rhamnopyranosyl)-(1->3)-4,6-O-benzylidene-2-phthalimido-β-D-glucopyranoside 
• 864815-53-2 methyl (2,3,4-tri-O-benzyl-α-L-mannopyranosyluronyl)-(1->3)-(4-O-benzyl-2-chloro-2-deoxy-α-L-rhamnopyranosyl)-(1->3)-2-(3-aminopropionamido)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside lactam 
• 864815-49-6 methyl (3-O-benzoyl-4-O-benzyl-2-chloro-2-deoxy-α-L-rhamnopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 864815-50-9 methyl (4-O-benzyl-2-chloro-2-deoxy-α-L-rhamnopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 864815-46-3 ethyl 3-O-benzoyl-4-O-benzyl-2-chloro-2-deoxy-1-thio-α-L-rhamnopyranoside 

Relevant articles and documents

Antibody-oligosaccharide interactions: the synthesis of 2-deoxy-&α-L-rhamnose containing oligosaccharide haptens related to Shigella flexneri variant Y antigen

A series of di-and trisaccharide glycosides based on the α-L-Rha(1->3)β-D-GlcNAc and α-L-Rha(1->3)α-L-Rha(1->3)β-D-GlcNAc elements have been synthesized to locate the minimal oligosaccharide determinant of the Shigella flexneri O-polysaccharide, which is built from a tetrasaccharide repeating unit, 2) α-L-Rhap(1->2)α-L-Rhap(1->3)α-L-Rhap(1->3)β-D-GlcNAcp(1->n.These compounds are also serve to identify the carbohydrate surface of the Shigella antigen that interacts with a monoclonal antibody, currently the subject of crystallographic studies.Two strategies utilizing suitably protected glycals 1 and 19 were employed to obtain analogs bearing either terminal od glycosylated 2,6-dideoxy-α-L-arabino-hexopyranosyl (2-deoxy-α-L-rhamnopyranosyl) residues.N-Iodosuccinimide activation of the glycals in the presence of selectively protected mono- and disaccharide alcohols afforded 2-deoxy-2-iodo-α-L-rhamnopyranosides and these were ultimately reduced during deprotection stages to afford the desired functionality.Di-O-acetyl L-rhamnal 1 reacted with monosaccharides 2 and 7, and with disaccharide 11, to yield disaccharides 4 and 8, and trisaccharide 12, each bearing a terminal 2-deoxy-α-L-rhamnopyranosyl residue.The selectively protected 3-O-benzoyl-4-O-benzyl-L-rhamnal 19 was synthesized from L-rhamnal and used to prepared trisaccharide 22, which contained an internal 2-deoxy-2-iodo-α-L-rhamnopyranosyl unit.Removal of protecting groups gave the oligosaccharides 6, 10, 14, and 23.Oligosaccharides that contained a 2-deoxy-α-L-rhamnopyranosyl residue showed enhanced inhibitory power: in the case of trisaccharide 23 a 1.8 kcal mol-1 relative increase in free energy of binding compared to a larger pentasaccharide epitope, α-L-Rhap(1->2)α-L-Rhap(1->3)α-L-Rhap(1->3)β-GlcAcp(1->2)α-L-Rhap-1->OMe.These data suggest that the rhamnose O-2 hydroxyl of residue C points toward and has important interactions with bindinbg site amino acids.