64650-81-3

Basic information

• Product Name: allyl α-L-rhamnopyranoside
• Synonyms: allyl α-L-rhamnopyranoside
• CAS NO: 64650-81-3
• Molecular Weight: 204.223
• Mol File: 64650-81-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: allyl α-L-rhamnopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: allyl α-L-rhamnopyranoside(64650-81-3)
• EPA Substance Registry System: allyl α-L-rhamnopyranoside(64650-81-3)

Safety Data

• Hazardous Substances Data: 64650-81-3(Hazardous Substances Data)

Upstream product

• 6155-35-7 L-rhamnose monohydrate 
• 107-18-6 allyl alcohol 

Downstream Products

• 197916-07-7 2-allyloxy-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran 
• 83866-10-8 (2S,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl 2,2,2-trichloroacetimidate 
• 86795-38-2 2,3,4-tri-O-(phenylmethyl)-α-L-rhamnopyranoside 
• 197916-17-9 (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranose 
• 197916-09-9 allyl (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranoside 
• 197916-18-0 (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranose 1-trichloroacetimidate 
• 127085-15-8 ((3aR,4R,6S,7S,7aS)-4-Allyloxy-6-methyl-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-tert-butyl-dimethyl-silane 
• 127875-17-6 Acetic acid (2S,3S,4R,5R,6R)-4,5-bis-benzyloxy-6-hydroxy-2-methyl-tetrahydro-pyran-3-yl ester 
• 138825-06-6 Acetic acid (2S,3S,4R,5R,6R)-4,5-bis-benzyloxy-2-methyl-6-[((E)-propenyl)oxy]-tetrahydro-pyran-3-yl ester 
• 127102-20-9 allyl 2,3-O-benzyl-4-O-tertbutyldimethylsilyl-α-L-rhamnopyranoside 
• 127085-19-2 (2S,3S,4R,5R,6S)-6-((2S,3S,4R,5R,6R)-6-Allyloxy-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-ol 
• 138824-95-0 Acetic acid (2S,3S,4R,5R,6S)-6-((2S,3S,4R,5R,6R)-6-allyloxy-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yl ester 
• 138824-97-2 Acetic acid (2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-6-[(2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-6-((2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-6-chloro-2-methyl-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester 
• 127085-21-6 (2S,3S,4R,5R,6S)-6-[(2S,3S,4R,5R,6S)-6-((2S,3S,4R,5R,6R)-6-Allyloxy-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-ol 

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.