346435-18-5

Basic information

• Product Name: p-Methoxyphenyl (methyl 2,3-di-O-acetyl-4-O-methyl-α-D-glucopyranosyluronate)-(1->2)-(3,4-O-di-acetyl-β-D-xylopyranosyl)-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside
• Synonyms: p-Methoxyphenyl (methyl 2,3-di-O-acetyl-4-O-methyl-α-D-glucopyranosyluronate)-(1->2)-(3,4-O-di-acetyl-β-D-xylopyranosyl)-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside
• CAS NO: 346435-18-5
• Molecular Weight: 968.917
• Mol File: 346435-18-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: p-Methoxyphenyl (methyl 2,3-di-O-acetyl-4-O-methyl-α-D-glucopyranosyluronate)-(1->2)-(3,4-O-di-acetyl-β-D-xylopyranosyl)-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: p-Methoxyphenyl (methyl 2,3-di-O-acetyl-4-O-methyl-α-D-glucopyranosyluronate)-(1->2)-(3,4-O-di-acetyl-β-D-xylopyranosyl)-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside(346435-18-5)
• EPA Substance Registry System: p-Methoxyphenyl (methyl 2,3-di-O-acetyl-4-O-methyl-α-D-glucopyranosyluronate)-(1->2)-(3,4-O-di-acetyl-β-D-xylopyranosyl)-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside(346435-18-5)

Safety Data

• Hazardous Substances Data: 346435-18-5(Hazardous Substances Data)

Upstream product

• 346435-16-3 p-Methoxyphenyl (methyl 2,3-di-O-benzyl-4-O-methyl-α-D-glucopyranosyluronate)-(1->2)-[3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-β-D-xylopyranosyl]-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside 
• 346434-97-7 p-Methoxyphenyl [2-O-chloroacetyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-β-D-xylopyranosyl]-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside 
• 346434-99-9 p-Methoxyphenyl [3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-β-D-xylopyranosyl]-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside 
• 346435-04-9 Ethyl 2,3-di-O-benzyl-6-O-triphenylmethyl-1-thio-β-D-glucopyranoside 
• 346434-93-3 p-Methoxyphenyl 2,3-di-O-benzoyl-β-D-xylopyranoside 
• 346435-08-3 methyl (ethyl 2,3-di-O-benzyl-4-O-methyl-1-thio-β-D-glucopyranoside)uronate 
• 346434-95-5 Ethyl 2-O-chloroacetyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-xylopyranoside 
• 346434-92-2 p-Methoxyphenyl 4-O-chloroacetyl-β-D-xylopyranoside 
• 1054666-85-1 (2S,3S,4aR,7S,8R,8aR)-7-Ethylsulfanyl-2,3-dimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-8-ol 
• 152964-70-0 ethyl 2,3-di-O-benzyl-1-thio-β-D-glucopyranoside 
• 13299-09-7 p-Methoxyphenyl β-D-xylopyranoside 
• 13299-05-3 p-Methoxyphenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside 
• 2595-46-2 ethyl 1-thio-β-D-xylopyranoside 

Relevant articles and documents

Synthesis of uronic acid-containing xylans found in wood and pulp

Two uronic acid-containing trisaccharides, (4-deoxy-β-L-threo-hex-4-enopyranosyluronic acid)- and (4-O-methyl-α-D-gluropyranosyluronic acid)-(1→2)-β-D-xylopyranosyl-(1→4)-D-xylopyranose, found in enzyme hydrolysates from pulp are synthesised. A common dixyloside 2′-OH acceptor, p-methoxyphenyl[3,4-O-(2′,3′-dimethoxybutane-2′,3′- diyl)-β-D-xylopyranosyl]-(1→4)-2,3-di-O-benzoyl-β- D-xylopyranoside, is constructed and coupled with two glucuronate thioglycoside donors differently substituted in the 4-position, O-methyl and O-mesyl, respectively, to give trisaccharides. DMTST as promoter in diethyl ether gives exclusively the α-linked products in high yield. Treatment of the 4″-O-mesyl trisaccharide with DBU then gives the α,β-unsaturated uronic acid derivative. The protection pattern introduced in the acceptor allows continued synthesis of larger oligosaccharides. Removal of the butanedione acetal produces 3′,4′-acceptors, and the p-methoxyphenyl glycoside can be transformed into various glycosyl donors, e.g. thioglycosides and sugar halides. Complete deprotection gives the two target reducing trisaccharides.