18403-12-8

Basic information

• Product Name: Benzyl-a-D-xylopyranoside
• Synonyms: Benzyl-a-D-xylopyranoside;NSC 170150;Benzyl alpha-D-xyloside;Benzyl alpha-D-xylopyranoside
• CAS NO: 18403-12-8
• Molecular Formula: C₁₂H₁₆O₅
• Molecular Weight: 240.25244
• Mol File: 18403-12-8.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 418.5°Cat760mmHg
• Flash Point: 206.9°C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 9.41E-08mmHg at 25°C
• Refractive Index: 1.597
• CAS DataBase Reference: Benzyl-a-D-xylopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl-a-D-xylopyranoside(18403-12-8)
• EPA Substance Registry System: Benzyl-a-D-xylopyranoside(18403-12-8)

Safety Data

• Hazardous Substances Data: 18403-12-8(Hazardous Substances Data)

Usage

General Description

Benzyl-α-D-xylopyranoside is a chemical compound that belongs to the class of xylose derivatives. It is a benzyl glycoside, which means it contains a xylose sugar molecule bonded to a benzyl group. Benzyl-a-D-xylopyranoside is often used in organic synthesis as a glycosylation reagent, where it can be used to introduce xylose moieties into other molecules. Benzyl-α-D-xylopyranoside has also been studied for its potential anti-inflammatory properties, as well as its ability to inhibit the growth of certain cancer cells. Overall, this compound has versatile applications in both chemical and biological research.

InChI:InChI=1/C12H16O5/c13-9-7-17-12(11(15)10(9)14)16-6-8-4-2-1-3-5-8/h1-5,9-15H,6-7H2

Upstream product

• 58-86-6 D-xylose 
• 100-51-6 benzyl alcohol 
• 87-72-9 D-Xylose 
• 1114-34-7 D-lyxose 
• 5328-37-0 L-arabinose 
• 87-72-9 L-arabinofuranose 
• 100-39-0 benzyl bromide 
• 6763-34-4 D-xylose 

Downstream Products

• 18403-20-8 benzyl 2-O-benzoyl-α-D-xylopyranoside 
• 219906-49-7 benzyl 2-O-(4-methoxybenzoyl)-α-D-xylopyranoside 
• 469860-87-5 benzyl β-D-galactopyranosyl-(1,4)-α-D-xylopyranoside 
• 99388-84-8 (2S,3R,4R,5R)-5-Allyloxy-2-benzyloxy-tetrahydro-pyran-3,4-diol 
• 99388-82-6 C₂₁H₂₈O₅ 
• 99388-83-7 (2S,3R,4S,5R)-5-Allyloxy-2,3,4-tris-benzyloxy-tetrahydro-pyran 
• 99388-75-7 Benzyl 4-O-(3-O-acetyl-2,4-di-O-benzyl-α-D-xylopyranosyl)-2,3-di-O-benzyl-α-D-xylopyranoside 
• 99388-76-8 Benzyl 4-O-(3-O-benzoyl-2,4-di-O-benzyl-α-D-xylopyranosyl)-2,3-di-O-benzyl-α-D-xylopyranoside 
• 99388-77-9 Benzyl O-(2,3,4-tri-O-benzyl-α-L-arabinofuranosyl)-(1-3)-O-(2,4-di-O-benzyl-β-D-xylopyranosyl)-(1-4)-2,3-di-O-benzyl-α-D-xylopyranoside 
• 99388-73-5 Benzyl 4-O-(2,4-di-O-benzyl-β-D-xylopyranosyl)-2,3-di-O-benzyl-α-D-xylopyranoside 
• 99388-74-6 Benzyl 4-O-(2,4-di-O-benzyl-α-D-xylopyranosyl)-2,3-di-O-benzyl-α-D-xylopyranoside 
• 99388-72-4 Benzyl 4-O-(3-O-Allyl-2,4-di-O-benzyl-β-D-xylopyranosyl)-2,3-di-O-benzyl-α-D-xylopyranoside 
• 99388-71-3 Benzyl 4-O-(3-O-Allyl-2,4-di-O-benzyl-α-D-xylopyranosyl)-2,3-di-O-benzyl-α-D-xylopyranoside 
• 889874-12-8 Benzyl 2,3-di-O-benzyl-α-D-xylopyranoside 

Relevant articles and documents

Regiospecific synthesis of lactose analog Gal-(β 1,4)-Xyl by transgalactosylation

A short enzymatic synthesis of disaccharide 4-O-β-D-galactopyranosyl-D-xylose (1) has been developed, which is of interest as a lactose analog for a non-invasive medicinal determination of lactose intolerance. The starting material, benzyl α-D-xyloside, was obtained by a Fischer-type glycosidation of D-xylose with benzyl alcohol, followed by anomeric differentiation of mixed glycosides using a glycosidase from Aspergillus oryzae. From several commercial β-galactosidases, which were screened for their transgalactosylation capacity, the enzyme from Escherichia coli was found to catalyze a virtually regio- and stereospecific galactosyl transfer from donor compounds o-nitrophenyl β-D-galactoside or lactose to the α-D-xyloside. Subsequent hydrogenolytic deprotection furnished desired disaccharide 1.

A Rapid and Mild Sulfation Strategy Reveals Conformational Preferences in Therapeutically Relevant Sulfated Xylooligosaccharides

Although sulfated xylooligosaccharides are promising therapeutic leads for a multitude of afflictions, the structural complexity and heterogeneity of commercially deployed forms (e. g. Pentosan polysulfate 1) complicates their path to further clinical development. We describe herein the synthesis of the largest homogeneous persulfated xylooligomers prepared to date, comprising up to eight xylose residues, as standards for biological studies. Near quantitative sulfation was accomplished using a remarkably mild and operationally simple protocol which avoids the need for high temperatures and a large excess of the sulfating reagent. Moreover, the sulfated xylooligomer standards so obtained enabled definitive identification of a pyridinium contaminant in a sample of a commercially prepared Pentosan drug and provided significant insights into the conformational preferences of the constituent persulfated monosaccharide residues. As the spatial distribution of sulfates is a key determinant of the binding of sulfated oligosaccharides to endogenous targets, these findings have broad implications for the advancement of Pentosan-based treatments.

Novel D-xylose derivatives stimulate muscle glucose uptake by activating AMP-activated protein kinase α

Type 2 diabetes mellitus has reached epidemic proportions; therefore, the search for novel antihyperglycemic drugs is intense. We have discovered that D-xylose increases the rate of glucose transport in a non-insulin-dependent manner in rat and human myot