4257-95-8

Basic information

• Product Name: 1,2,3,4-tri-O-acetyl-α-D-ribopyranose
• Synonyms: 1,2,3,4-tri-O-acetyl-α-D-ribopyranose
• CAS NO: 4257-95-8
• Molecular Weight: 318.281
• Mol File: 4257-95-8.mol
• Article Data: 79

Chemical Properties

• CAS DataBase Reference: 1,2,3,4-tri-O-acetyl-α-D-ribopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-tri-O-acetyl-α-D-ribopyranose(4257-95-8)
• EPA Substance Registry System: 1,2,3,4-tri-O-acetyl-α-D-ribopyranose(4257-95-8)

Safety Data

• Hazardous Substances Data: 4257-95-8(Hazardous Substances Data)

Upstream product

• 87-72-9 L-(+)-arabinose 
• 108-24-7 acetic anhydride 
• 5328-37-0 L-arabinose 
• 7296-56-2 β-L-arabinopyranose 
• 87-72-9 D-Xylose 
• 58-86-6 D-xylose 
• 10257-32-6 D-ribose 
• 50-69-1 D-ribose 
• 127-09-3 sodium acetate 
• 110-86-1 pyridine 
• 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 
• 41546-21-8 L-ribose 

Downstream Products

• 4049-33-6 tetra-O-acetyl-β-D-xylopyranose 
• 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) 
• 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 
• 1141-01-1 phenyl β-L-arabinopyranoside 

Relevant articles and documents

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.

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