144174-52-7

Basic information

• Product Name: allyl 4-O-benzyl-3-O-para-methoxybenzyl-α-L-rhamnopyranoside
• Synonyms: allyl 4-O-benzyl-3-O-para-methoxybenzyl-α-L-rhamnopyranoside
• CAS NO: 144174-52-7
• Molecular Weight: 414.499
• Mol File: 144174-52-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: allyl 4-O-benzyl-3-O-para-methoxybenzyl-α-L-rhamnopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: allyl 4-O-benzyl-3-O-para-methoxybenzyl-α-L-rhamnopyranoside(144174-52-7)
• EPA Substance Registry System: allyl 4-O-benzyl-3-O-para-methoxybenzyl-α-L-rhamnopyranoside(144174-52-7)

Safety Data

• Hazardous Substances Data: 144174-52-7(Hazardous Substances Data)

Upstream product

• 2746-25-0 p-Methoxybenzyl bromide 
• 818-08-6 di(n-butyl)tin oxide 
• 89821-78-3 allyl 4-O-benzyl-α-L-rhamnopyranoside 
• 824-94-2 p-methoxybenzyl chloride 
• 73-34-7 L-rhamnose 
• 475672-25-4 allyl L-rhamnopyranoside 

Downstream Products

• 144174-53-8 allyl 2-O-allyl-4-O-benzyl-3-O-p-methoxybenzyl-α-L-rhamnopyranoside 
• 144174-54-9 (2R,3R,4R,5R,6S)-2,3-Bis-allyloxy-5-benzyloxy-6-methyl-tetrahydro-pyran-4-ol 
• 144174-55-0 Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-2-((2R,3R,4R,5S,6S)-2,3-bis-allyloxy-5-benzyloxy-6-methyl-tetrahydro-pyran-4-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester 
• 1349065-21-9 allyl 4-O-benzyl-2-O-chloroacetyl-3-O-para-methoxybenzyl-α-L-rhamnopyranoside 
• 1349064-78-3 allyl 2-O-(2-(azidomethyl)benzoyl)-4-O-benzyl-3-O-para-methoxybenzyl-α-L-rhamnopyranoside 
• 1349064-63-6 2-O-(2-(azidomethyl)benzoyl)-4-O-benzyl-3-O-para-methoxybenzyl-α-L-rhamnopyranosyl trichloroacetimidate 
• 1349064-65-8 4-O-benzyl-2-O-chloroacetyl-3-O-para-methoxybenzyl-α-L-rhamnopyranosyl trichloroacetimidate 
• 1448429-77-3 allyl 4-O-benzyl-2-O-levulinoyl-3-O-p-methoxybenzyl-α-L-rhamnopyranoside 
• 1448430-11-2 4-O-benzyl-2-O-levulinoyl-3-O-p-methoxybenzyl-α-L-rhamnopyranose 
• 1448430-12-3 4-O-benzyl-2-O-levulinoyl-3-O-p-methoxybenzyl-β-L-rhamnopyranose 

Relevant articles and documents

Glycoconjugates and their use as potential vaccines against infection by Shigella Flexneri

The present invention relates to a conjugate comprising an oligo- or polysaccharide selected from the group consisting of: ???????? (X)x-{BCDA}n-(Y)y ???????? (X)x-{CDAB}n-(Y)y ???????? (X)

Concise synthesis of di- and trisaccharides related to the O-antigens from Shigella flexneri serotypes 6 and 6a, based on late stage mono-O-acetylation and/or site-selective oxidation

Shigella flexneri serotypes 6 and 6a are closely related bacteria causing shigellosis in humans. Their O-antigens are {→4)-β-d-GalpA-(1→3)- β-d-GalpNAc-(1→2)-[3Ac/4Ac]-α-l-Rhap-(1→2) -α-l-Rhap-(1→}n acidic polysaccharides ({AB AcCD}n), which only differ in the degree of O-acetylation. A concise synthesis of two disaccharides (BC, BAcC) and four trisaccharides, representing portions and/or analogs of the O-antigens, is described. A protected intermediate compatible with late stage 3 C-O-acetylation, and/or galactosyl (A) to galacturonic acid (A) conversion, was designed and assembled from trichloroacetimidate and thioglycoside donors tuned for high yielding glycosylation and excellent stereocontrol. The galacturonic moiety was efficiently introduced from galactose using a TEMPO/NaOCl/NaClO2-based oxidation protocol optimized for full compatibility with sensitive moieties, such as allyl ethers and acetates. Final Pd/C-mediated deprotection provided the targets, including the propyl glycoside ABAcC, its non O-acetylated counterpart ABC, and the non acidic analogs A BAcC and A BC. The BC and ABC oligosaccharides are also portions of the O-antigen from Escherichia coli O147, which causes diarrhea in pigs.

Synthesis of methyl 3-o-[3-o-(2,3,4-tri-o-methyl-α-L-rhamnopyranosyl)-α-L- rhamnopyranosyl]-α-L-rhamnopyranoside : The outer trisaccharide unit of a unique Mycobacterium xenopi glycopeptidolipid

The combination of sugars present in Mycobecterium xenopi glycopeptido-lipid (GPL X-1) has been characterised as O-(2,3,4-tri-O-methyl-α-L-rhamnopyranosyl)-(1-3)-O-(α-L- rhamnopyranosyl)-(1-3)-O-(α-L-rhamnopyranosyl)-(1-3)-6-deoxy-L-glucose. Two synthetic