25243-38-3

Basic information

• Product Name: 1,2,3,4-tetra-O-acetyl-β-D-arabinopyranose
• Synonyms: 1,2,3,4-tetra-O-acetyl-β-D-arabinopyranose
• CAS NO: 25243-38-3
• Molecular Weight: 318.281
• Mol File: 25243-38-3.mol
• Article Data: 81

Chemical Properties

• CAS DataBase Reference: 1,2,3,4-tetra-O-acetyl-β-D-arabinopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-tetra-O-acetyl-β-D-arabinopyranose(25243-38-3)
• EPA Substance Registry System: 1,2,3,4-tetra-O-acetyl-β-D-arabinopyranose(25243-38-3)

Safety Data

• Hazardous Substances Data: 25243-38-3(Hazardous Substances Data)

Upstream product

• 28697-53-2 D-arabinopyranose 
• 108-24-7 acetic anhydride 
• 7601-90-3 perchloric acid 
• 64-19-7 acetic acid 
• 4049-33-6 tetra-O-acetyl-β-D-xylopyranose 
• 7664-93-9 sulfuric acid 
• 87-72-9 D-Xylose 
• 4258-00-8 1,2,3,4-tetra-O-acetyl-β-L-arabinopyranose 
• 87-72-9 L-(+)-arabinose 
• 10323-20-3 D-Arabinose 
• 32453-58-0 methyl-2,3,4-tri-O-acetyl-6-deoxy-β-L-glucopyranoside 
• 32453-59-1 (2R,3S,4R,5R)-2-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1195726-04-5 trans-2-ethoxy-3,4-epoxytetrahydropyran 
• 31080-85-0 trans-6-ethoxy-5-hydroxy-5,6-dihydro-2H-pyran 

Downstream Products

• 19186-37-9 1,2,3,4-tetra-O-acetyl-α-D-arabinopyranose 
• 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 
• 75247-31-3 α-1-bromo-1-deoxy-2,3,4-tri-O-acetyl-L-arabinopyranose 
• 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 

Relevant articles and documents

Stereoselective acetylation of hemicellulosic C5-sugars

The stereoselective peracetylation of α-D-xylose (1) and α-L-arabinose (4) using a combination of triethylamine and acetic anhydride in the presence or absence of a catalytic amount of dimethylaminopyridine (DMAP) is described. The peracetylated D-xylose and L-arabinose alpha pyranose anomers 2α and 5α are obtained in 97% and 56% yields respectively. The peracetylated D-xylose beta pyranose anomer 2β is obtained in 71% yield through simple modification of the reaction conditions. Details regarding synthesis and isolation optimization studies under different conditions are presented below. The stereoselective peracetylation reactions disclosed here have been used to separate mixtures of D-xylose and L-arabinose as their peracetylated derivatives 2β and 5α in 47% and 42% yields and can provide pure pentoses after deacetylation.

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.

Isolation and characterization of triterpenoid saponins from leaves of Aralia nudicaulis L

Three new oleanolic glycosides (1–3), along with seven known saponins from various plants (4–10) were isolated for the first time from the leaves of Aralia nudicaulis. Their structures were elucidated on the basis of spectroscopic evidence, including 1D and 2D NMR, and HRESIMS. Nudicauloside A and B (1–2) have shown moderate anti-inflammatory activity, as demonstrated by inhibition of LPS-induced NO production in raw 264.7 murine macrophages (IC50 = 74–101 μM).