109714-40-1

Basic information

• Product Name: allyl 3-O-<2'-O-(2''-O-acetyl-3'',4''-di-O-benzyl-α-L-rhamnopyranosyl)-3',4'-di-O-benzyl-α-L-rhamnopyranosyl>-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside
• Synonyms: allyl 3-O-<2'-O-(2''-O-acetyl-3'',4''-di-O-benzyl-α-L-rhamnopyranosyl)-3',4'-di-O-benzyl-α-L-rhamnopyranosyl>-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside
• CAS NO: 109714-40-1
• Molecular Weight: 1093.28
• Mol File: 109714-40-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: allyl 3-O-<2'-O-(2''-O-acetyl-3'',4''-di-O-benzyl-α-L-rhamnopyranosyl)-3',4'-di-O-benzyl-α-L-rhamnopyranosyl>-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: allyl 3-O-<2'-O-(2''-O-acetyl-3'',4''-di-O-benzyl-α-L-rhamnopyranosyl)-3',4'-di-O-benzyl-α-L-rhamnopyranosyl>-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside(109714-40-1)
• EPA Substance Registry System: allyl 3-O-<2'-O-(2''-O-acetyl-3'',4''-di-O-benzyl-α-L-rhamnopyranosyl)-3',4'-di-O-benzyl-α-L-rhamnopyranosyl>-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside(109714-40-1)

Safety Data

• Hazardous Substances Data: 109714-40-1(Hazardous Substances Data)

Upstream product

• 72599-87-2 2-O-acetyl-3,4-di-O-benzyl-6-deoxy-α-L-mannopyranosyl chloride 
• 109744-29-8 allyl 2-O-benzoyl-4-O-benzyl-3-O-(3',4'-di-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside 
• 64650-81-3 allyl α-L-rhamnopyranoside 
• 109714-38-7 allyl 2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside 
• 100-39-0 benzyl bromide 
• 6155-35-7 L-rhamnose monohydrate 
• 89821-78-3 allyl 4-O-benzyl-α-L-rhamnopyranoside 
• 109714-39-8 allyl 3-O-(2'-O-acetyl-3',4'-di-O-benzyl-α-L-rhamnopyranosyl)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside 
• 707-07-3 orthobenzoic acid trimethyl ester 

Downstream Products

• 109744-31-2 C₆₅H₇₂O₁₅ 
• 109714-42-3 3-O-<2'-O-(2''-O-acetyl-3'',4''-di-O-benzyl-α-L-rhamnopyranosyl)-3',4'-di-O-benzyl-α-L-rhamnopyranosyl>-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl chloride 
• 109714-41-2 3-O-<2'-O-(2''-O-acetyl-3'',4''-di-O-benzyl-α-L-rhamnopyranosyl)-3',4'-di-O-benzyl-α-L-rhamnopyranosyl>-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranose 

Relevant articles and documents

Synthesis of Oligosaccharides Corresponding to Biological Repeating Units of Shigella flexneri Variant Y Polysaccharide. Part 1. Overall Strategy, Synthesis of a Key Trisaccharide Intermediate, and Synthesis of a Pentasaccharide

The overall strategy for the synthesis of penta- up to octa-saccharides, representing the biological repeating unit of the Shigella flexneri serogroup Y lipopolysaccharide, is described.The key intermediate, the common terminal trisaccharide, α-L-Rhap-(1->2)-α-L-Rhap(1->3)-α-L-Rhap, has been synthesised by a series of Koenigs-Knorr reactions.A selectively protected rhamnose intermediate has been developed for the synthesis of this trisaccharide as its allyl glycoside.Allyl α-L-rhamnopyranoside was converted into the corresponding 2-O-benzoyl-4-O-benzyl derivative via a 2,3-orthobenzoate.Koenigs-Knorr reaction between this partially blocked rhamnoside and 2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl chloride afforded the blocked disaccharide.Selective transesterification of the 2'-O-acetyl group in the presence of the 2-O-benzoate yielded the disaccharide, selectively deblocked at the C-2' position.Reaction with the same rhamnopyranosyl chloride gave the fully blocked trisaccharide.Deallylation, followed by treatment with NN-dimethyl(chloromethylene)ammonium chloride, then gave the corresponding trisaccharide chloride.In conjunction with the disaccharide methyl 2-O-(2'-acetamido-4',6'-O-benzylidene-2'-deoxy-β-D-glucopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranoside, the synthesis of the blocked pentasaccharide was accomplished.Transesterification, followed by hydrogenolysis in aqueous acetic acid, afforded the pure pentasaccharide hapten, α-L-Rhap-(1->2)-α-L-Rhap-(1->3)-α-L-Rhap-(1->3)-β-D-GlcpNAc-(1->2)-α-L-Rhap, as its methyl glycoside, for use in binding studies and n.m.r. studies.