4049-33-6

Basic information

• Product Name: 1,2,3,4-TETRA-O-ACETYL-BETA-D-XYLOPYRANOSE
• Synonyms: BETA D-XYLOSE TETRAACETATE;1,2,3,4-TETRA-O-ACETYL-BETA-D-XYLOPYRANOSE;1,2,3,4-Tetra-O-acetyl-b-D-xylopyranose;1,2,3,4-TETRA-O-ACETYL-SS-D-XYLOPYRANOSE;beta-D-Xylopyranose tetraacetate;xylose tetraacetate;b-D-Xylopyranose,1,2,3,4-tetraacetate;1,2,3,4-Tetra-O-acetyl-D-xylopyranose(β forM)
• CAS NO: 4049-33-6
• Molecular Formula: C₁₃H₁₈O₉
• Molecular Weight: 318.28
• EINECS: 200-258-5
• Mol File: 4049-33-6.mol
• Article Data: 105

Chemical Properties

• Melting Point: 123-125 °C
• Boiling Point: 362.9 °C at 760 mmHg
• Flash Point: 157 °C
• Appearance: /
• Density: 1.29 g/cm³
• Vapor Pressure: 1.87E-05mmHg at 25°C
• Refractive Index: 1.475
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 1,2,3,4-TETRA-O-ACETYL-BETA-D-XYLOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-TETRA-O-ACETYL-BETA-D-XYLOPYRANOSE(4049-33-6)
• EPA Substance Registry System: 1,2,3,4-TETRA-O-ACETYL-BETA-D-XYLOPYRANOSE(4049-33-6)

Safety Data

• Hazardous Substances Data: 4049-33-6(Hazardous Substances Data)

Usage

Description

1,2,3,4-Tetra-O-acetyl-beta-D-xylopyranose is a carbohydrate chemical compound derived from beta-D-xylopyranose, a five-membered ring sugar molecule. It is acetylated at all four hydroxyl groups of the xylose ring, enhancing its stability and resistance to hydrolysis. This versatile compound is widely used as a reagent in organic synthesis and as a building block for the synthesis of pharmaceutical compounds and natural products. The selective removal of acetyl groups allows access to free hydroxyl groups for further chemical reactions, making it valuable in various industries such as pharmaceuticals, agrochemicals, and biotechnology.

Uses

Used in Pharmaceutical Industry:
1,2,3,4-Tetra-O-acetyl-beta-D-xylopyranose is used as a building block for the synthesis of various pharmaceutical compounds and natural products. Its acetylated structure provides stability and resistance to hydrolysis, making it suitable for the development of new drugs and therapeutic agents.
Used in Organic Synthesis:
1,2,3,4-Tetra-O-acetyl-beta-D-xylopyranose is used as a reagent in organic synthesis. Its selective removal of acetyl groups allows access to free hydroxyl groups, enabling further chemical reactions and the creation of diverse organic compounds.
Used in Agrochemical Industry:
1,2,3,4-Tetra-O-acetyl-beta-D-xylopyranose is utilized in the agrochemical industry for the synthesis of various agrochemical compounds. Its versatility and stability make it a valuable component in the development of new agrochemical products.
Used in Biotechnology:
1,2,3,4-Tetra-O-acetyl-beta-D-xylopyranose is employed in biotechnology for the synthesis of biologically active compounds and the development of novel bioprocesses. Its unique properties and reactivity contribute to the advancement of biotechnological applications.

InChI:InChI=1/C13H18O9/c1-6(14)19-10-5-18-13(22-9(4)17)12(21-8(3)16)11(10)20-7(2)15/h10-13H,5H2,1-4H3/t10-,11+,12-,13+/m1/s1

Upstream product

• 58-86-6 D-xylose 
• 7664-93-9 sulfuric acid 
• 108-24-7 acetic anhydride 
• 28697-53-2 D-arabinopyranose 
• 87-72-9 L-(+)-arabinose 
• 69534-64-1 (5S)-1,2,3,4-tetra-O-acetyl-5-bromo-β-D-xylopyranose 
• 107-13-1 acrylonitrile 
• 87-72-9 D-Xylose 
• 127-09-3 sodium acetate 
• 41546-21-8 L-ribose 
• 64-19-7 acetic acid 
• 1233-03-0 α-D-xylopyranose tetraacetate 
• 7601-90-3 perchloric acid 
• 68579-19-1 Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-(5,5-dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester 

Downstream Products

• 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 
• 53784-33-1 2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-D-xylopyranose 
• 34280-00-7 4-phenyl-1-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-1H-[1,2,3]triazole 
• 1415685-33-4 1-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-4-(4-nitrophenyl)-1,2,3-triazole 
• 1415685-34-5 1-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-4-(4-methylphenyl)-1,2,3-triazole 
• 1415685-35-6 1-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-1,2,3-triazole-4-(4-methoxy-2-methylphenyl)-1,2,3-triazole 
• 1415685-37-8 1-(β-D-xylopyranosyl)-4-(4-nitrophenyl)-1,2,3-triazole 
• 1415685-38-9 1-(β-D-xylopyranosyl)-4-(4-methylphenyl)-1,2,3-triazole 
• 1415685-39-0 1-(β-D-xylopyranosyl)-4-(4-methoxy-2-methylphenyl)-1,2,3-triazole 
• 94921-62-7 (4-nitro-phenyl)-(tri-O-acetyl-β-L-arabinopyranoside) 

Relevant articles and documents

Preparation of new β-D-xyloside- and β-D-xylobioside-based ionic liquids through chemical and/or enzymatic reactions

Several tetraalkylphosphonium and tetraalkylammonium salts containing xyloside- and xylobioside-based anionic moieties have been prepared. Two stereoselective routes have been developed: i) a chemical pathway in four steps from D-xylose, and ii) a chemoenzymatic pathway directly from biomass-derived xylans. These salts displayed interesting properties as ionic liquids. Their structures have been correlated to their thermal properties (melting, glass transition and decomposition temperatures).

Synthesis, surface properties, and biocompatibility of 1,2,3-triazole- containing alkyl β-D-xylopyranoside surfactants

We are interested in the development of surfactants derived from hemicellulosic biomass, as they are potential components in pharmaceuticals, personal care products, and other detergents. Such surfactants should exhibit low toxicity in mammalian cells. In this study we synthesized a series of alkyl or fluoroalkyl β-xylopyranosides from azides and an alkyne using the copper-catalyzed azide-alkyne (CuAAC) 'click' reaction in 4 steps from xylose. The purified products were evaluated for both their surfactant properties, and for their biocompatibility. Unlike other carbohydrate-based surfactants, liquid-crystalline behavior was not observed by differential scanning calorimetry. The triazole-containing β-xylopyranosides with short (6 carbons) and long (>12 carbons) chains exhibited no toxicity at concentrations ranging from 1 to 1000 μM. Triazole-containing β-xylopyranosides with 8, 10, or 12 carbons caused toxicity via apoptosis, with CC50 values ranging from 26-890 μM. The two longest chain compounds did form stable monolayers at the air-water interface over a range of temperatures, although a brief transition to an the unstable monolayer was observed.

Synthesis and biological evaluation of 3β-O-neoglycosides of caudatin and its analogues as potential anticancer agents

In order to study the structure–activity relationship (SAR) of C21-steroidal glycosides toward human cancer cell lines and explore more potential anticancer agents, a series of 3β-O-neoglycosides of caudatin and its analogues were synthesized. The results revealed that most of peracetylated 3β-O-monoglycosides demonstrated moderate to significant antiproliferative activities against four human cancer cell lines (MCF-7, HCT-116, HeLa, and HepG2). Among them, 3β-O-(2,3,4-tri-O-acetyl-β-L-glucopyranosyl)-caudatin (2k) exhibited the highest antiproliferative activity aganist HepG2 cells with an IC50 value of 3.11 μM. Mechanical studies showed that compound 2k induced both apoptosis and cell cycle arrest at S phase in a dose dependent manner. Overall, these present findings suggested that glycosylation is a promising scaffold to improve anticancer activity for naturally occurring C21-steroidal aglycones, and compound 2k represents a potential anticancer agent deserved further investigation.

Total Synthesis of (+)-Erogorgiaene and the Pseudopterosin A?F Aglycone via Enantioselective Cobalt-Catalyzed Hydrovinylation

Due to their pronounced bioactivity and limited availability from natural resources, metabolites of the soft coral Pseudopterogorgia elisabethae, such as erogorgiaene and the pseudopterosines, represent important target molecules for chemical synthesis. We have now developed a particularly short and efficient route towards these marine diterpenes exploiting an operationally convenient enantioselective cobalt-catalyzed hydrovinylation as the chirogenic step. Other noteworthy C?C bond forming transformations include diastereoselective Lewis acid-mediated cyclizations, a Suzuki coupling and a carbonyl ene reaction. Starting from 4-methyl-styrene the anti-tubercular agent (+)-erogorgiaene (>98 % ee) was prepared in only 7 steps with 46 % overall yield. In addition, the synthesis of the pseudopterosin A aglycone was achieved in 12 steps with 30 % overall yield and, surprisingly, was found to exhibit a similar anti-inflammatory activity (inhibition of LPS-induced NF-κB activation) as a natural mixture of pseudopterosins A?D or iso-pseudopterosin A, prepared by β-D-xylosylation of the synthetic aglycone.