1233-03-0

Basic information

• Product Name: .alpha.-Xylopyranose, tetraacetate
• Synonyms: .alpha.-Xylopyranose, tetraacetate
• CAS NO: 1233-03-0
• Molecular Formula: C₁₃H₁₈O₉
• Molecular Weight: 318.28
• Mol File: 1233-03-0.mol
• Article Data: 79

Chemical Properties

• Melting Point: 57-59 °C
• Boiling Point: 362.9±42.0 °C(Predicted)
• Appearance: /
• Density: 1.29±0.1 g/cm3(Predicted)
• CAS DataBase Reference: .alpha.-Xylopyranose, tetraacetate(CAS DataBase Reference)
• NIST Chemistry Reference: .alpha.-Xylopyranose, tetraacetate(1233-03-0)
• EPA Substance Registry System: .alpha.-Xylopyranose, tetraacetate(1233-03-0)

Safety Data

• Hazardous Substances Data: 1233-03-0(Hazardous Substances Data)

Usage

General Description

.alpha.-Xylopyranose, tetraacetate is a chemical compound that is formed by the acetylation of alpha-xylopyranose. It is a derivative of xylopyranose, which is a five-membered ring sugar molecule. The tetraacetate form has four acetyl groups attached to the xylopyranose ring. .alpha.-Xylopyranose, tetraacetate is often used in organic chemistry as a reagent for various chemical reactions. It has applications in the synthesis of other organic compounds and is also used as a building block for the creation of more complex molecules. The tetraacetate form of alpha-xylopyranose is a key intermediate in the production of various pharmaceuticals, agrochemicals, and other chemical products.

Upstream product

• 4049-33-6 tetra-O-acetyl-β-D-xylopyranose 
• 58-86-6 D-xylose 
• 108-24-7 acetic anhydride 
• 87-72-9 D-Xylose 
• 75-36-5 acetyl chloride 
• 7664-93-9 sulfuric acid 
• 4258-00-8 1,2,3,4-tetra-O-acetyl-β-L-arabinopyranose 
• 5328-37-0 L-arabinose 
• 87-72-9 L-(+)-arabinose 
• 7296-55-1 L-arabinose 
• 41546-21-8 L-ribose 
• 1195726-04-5 trans-2-ethoxy-3,4-epoxytetrahydropyran 
• 31080-85-0 trans-6-ethoxy-5-hydroxy-5,6-dihydro-2H-pyran 
• 10369-25-2 2,3,4-tri-O-acetyl-α,β-L-arabinopyranose 

Downstream Products

• 4049-33-6 tetra-O-acetyl-β-D-xylopyranose 
• 94921-62-7 (4-nitro-phenyl)-(tri-O-acetyl-β-L-arabinopyranoside) 
• 94921-63-8 (4-nitro-phenyl)-(tri-O-acetyl-α-L-arabinopyranoside) 
• 3456-62-0 2-methylphenyl-α-L-arabinopyranoside 
• 14227-90-8 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide 
• 76850-61-8 (2R,3R,4S,5S)-2-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-3,4,5-triol 
• 76898-75-4 (2R,3R,4S,5S)-2-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-3,4,5-triol 
• 169304-01-2 Acetic acid (2R,3R,4S,5R)-4,5-diacetoxy-2-(3-cyano-4,6-diphenyl-2-thioxo-2H-pyridin-1-yl)-tetrahydro-pyran-3-yl ester 
• 169304-03-4 Acetic acid (2R,3R,4S,5R)-4,5-diacetoxy-2-(3-cyano-4-phenyl-2-thioxo-6-p-tolyl-2H-pyridin-1-yl)-tetrahydro-pyran-3-yl ester 
• 169304-06-7 Acetic acid (2R,3R,4S,5R)-4,5-diacetoxy-2-(3-cyano-4-furan-2-yl-2-thioxo-6-p-tolyl-2H-pyridin-1-yl)-tetrahydro-pyran-3-yl ester 
• 169304-04-5 Acetic acid (2R,3R,4S,5R)-4,5-diacetoxy-2-[3-cyano-4-(4-methoxy-phenyl)-6-phenyl-2-thioxo-2H-pyridin-1-yl]-tetrahydro-pyran-3-yl ester 
• 169304-07-8 Acetic acid (2R,3R,4S,5R)-4,5-diacetoxy-2-[3-cyano-4-furan-2-yl-6-(4-methoxy-phenyl)-2-thioxo-2H-pyridin-1-yl]-tetrahydro-pyran-3-yl ester 
• 75247-31-3 α-1-bromo-1-deoxy-2,3,4-tri-O-acetyl-L-arabinopyranose 
• 943857-29-2 p-methoxyphenyl 2,3,4-tri-O-acetyl-α-L-arabinopyranoside 

Relevant articles and documents

Design, Synthesis, biological investigations and molecular interactions of triazole linked tacrine glycoconjugates as Acetylcholinesterase inhibitors with reduced hepatotoxicity

Tacrine is a known Acetylcholinesterase (AChE) inhibitors having hepatotoxicity as main liability associated with it. The present study aims to reduce its hepatotoxicity by synthesizing tacrine linked triazole glycoconjugates via Huisgen's [3 + 2] cycloaddition of anomeric azides and terminal acetylenes derived from tacrine. A series of triazole based glycoconjugates containing both acetylated (A-1 to A-7) and free sugar hydroxyl groups (A-8 to A-14) at the amino position of tacrine were synthesized in good yield taking aid from molecular docking studies and evaluated for their in vitro AChE inhibition activity as well as hepatotoxicity. All the hybrids were found to be non-toxic on HePG2 cell line at 200 μM (100 % cell viability) as compared to tacrine (35 % cell viability) after 24 h of incubation period. Enzyme kinetic studies carried out for one of the potent hybrids in the series A-1 (IC50 0.4 μM) revealed its mixed inhibition approach. Thus, compound A-1 can be used as principle template to further explore the mechanism of action of different targets involved in Alzheimer's disease (AD) which stands as an adequate chemical probe to be launched in an AD drug discovery program.

Synthesis of podophyllotoxin-glycosyl triazoles via click protocol mediated by silver (I)-N-heterocyclic carbenes and their anticancer evaluation as topoisomerase-II inhibitors

Herein we report the regioselective synthesis of podophyllotoxin-Glycosyl triazole hybrids catalysed by Ag(I)-N-heterocyclic carbene (Ag(I)-NHC) in a short reaction time (～30 min) at ambient conditions. In principle, it is the first report of Click alkyne-azide cycloaddition catalysed by Ag(I)-NHC catalyst and moreover, this new methodology yielded good results when compared with traditional CuAAC in terms of reaction time and selectivity. The synthesised compounds were further explored for in vitro anticancer activity against four human cancer cell lines Du145, HeLa, A-549, and MCF-7 and found that these synthesised compounds possess significant anticancer activity. Further, the compounds 5a and 5e were identified as promising leads due to their better activity across all cell lines than that of the standard drug etoposide. Molecular docking studies of 5a & 5e with DNA Topoisomerase-II were revealed that the free energy calculations of active compounds were in good agreement with observed IC50 values.

Protecting carbohydrates with ethers, acetals and orthoesters under basic conditions

Chlorinated ethyl and vinyl ethers are introduced at various positions of carbohydrates. Depending on the relative stereochemistry, vinylethers, acetals or orthoesters are formed under basic conditions. The products are stable, but are easily deprotected