13299-09-7

Basic information

• Product Name: p-Methoxyphenyl β-D-xylopyranoside
• Synonyms: p-Methoxyphenyl β-D-xylopyranoside
• CAS NO: 13299-09-7
• Molecular Weight: 256.255
• Mol File: 13299-09-7.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: p-Methoxyphenyl β-D-xylopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: p-Methoxyphenyl β-D-xylopyranoside(13299-09-7)
• EPA Substance Registry System: p-Methoxyphenyl β-D-xylopyranoside(13299-09-7)

Safety Data

• Hazardous Substances Data: 13299-09-7(Hazardous Substances Data)

Upstream product

• 3068-31-3 1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose 
• 87-72-9 D-Xylose 
• 128376-91-0 2,3,4-tri-O-acetyl-α-D-xylopyranosyl trichloroacetimidate 
• 106820-14-8 2,3,4-Tri-O-acetyl-D-xylopyranose 
• 62446-93-9 1,2,3,4-tetra-O-acetyl-D-xylopyranose 
• 4049-33-6 tetra-O-acetyl-β-D-xylopyranose 
• 150-76-5 4-methoxy-phenol 
• 2001-96-9 p-nitrophenyl β-D-xylopyranoside 
• 13299-05-3 p-Methoxyphenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside 

Downstream Products

• 475101-61-2 4-methoxyphenyl O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside 
• 475101-62-3 4-methoxyphenyl O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside 
• 721438-51-3 4-methoxyphenyl O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside 
• 475101-60-1 4-methoxyphenyl O-(2,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside 
• 475101-59-8 4-methoxyphenyl O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-galactopyranosyl)-(1->4)-β-D-xylopyranoside 
• 475101-58-7 4-methoxyphenyl 2,3-O-isopropylidene β-D-xylopyranoside 
• 346434-92-2 p-Methoxyphenyl 4-O-chloroacetyl-β-D-xylopyranoside 
• 144683-68-1 (2S,3R,4S,5R,6R)-2-[(3R,4R,5R,6S)-4,5-Dihydroxy-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 144683-67-0 (2S,3R,4S,5R,6R)-2-[(2S,3R,4S,5R)-3,5-Dihydroxy-2-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 2460-44-8 β-D-xylopyranoside 
• 150-76-5 4-methoxy-phenol 

Relevant articles and documents

Total Synthesis of Pseudomonas aeruginosa 1244 Pilin Glycan via de Novo Synthesis of Pseudaminic Acid

Pseudaminic acid (Pse) is a nonulosonic acid unique to bacterial species, found as a component of important cell surface glycans and glycoproteins in various pathogenic species, such as the critical hospital threat Pseudomonas aeruginosa. Herein we present the development of a facile and scalable de novo synthesis of Pse and its functionalized derivatives from easily available Cbz-l-allo-threonine methyl ester (16 steps in 11% yield). The key reactions in our de novo synthesis involve the diastereoselective glycine thioester isonitrile-based aldol-type reaction to create the 1,3-anti-diamino skeleton, followed by the Fukuyama reduction and the indium-mediated Barbier-type allylation. Moreover, we have studied the glycosylation of the Pse glycosyl donors and identified the structural determinants for its glycosylation diastereoselectivity, which enabled us to complete the total synthesis of P. aeruginosa 1244 pilin trisaccharide α-5NβOHC47NFmPse-(2→4)-β-Xyl-(1→3)-FucNAc.

Synthetic approach toward the partial sequences of betaglycan in the linkage region on solid support and in solution phase

We have synthesized, for the first time, the partial sequence of the betaglycan composed of the tetraosyl hexapeptide, which was directly usable as a probe for enzymatic glycosyl transfer. Stepwise elongation afforded the corresponding tetraosyl trichloro

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.