52544-91-9

Basic information

• Product Name: phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-arabinopyranoside
• CAS NO: 52544-91-9
• Molecular Weight: 368.408
• Mol File: 52544-91-9.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-arabinopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-arabinopyranoside(52544-91-9)
• EPA Substance Registry System: phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-arabinopyranoside(52544-91-9)

Safety Data

• Hazardous Substances Data: 52544-91-9(Hazardous Substances Data)

Upstream product

• 3111-52-2 potassium thiophenolate 
• 3068-29-9 2,3,4-tri-O-acetyl-β-D-arabinosyl bromide 
• 108-98-5 thiophenol 
• 3068-31-3 1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose 
• 4049-33-6 tetra-O-acetyl-β-D-xylopyranose 
• 14227-90-8 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide 
• 158419-93-3 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl thiocyanate 
• 26905-22-6 hydroxymethyl phenyl sulfide 
• 128376-91-0 2,3,4-tri-O-acetyl-α-D-xylopyranosyl trichloroacetimidate 
• 62446-93-9 1,2,3,4-tetra-O-acetyl-D-xylopyranose 
• 930-69-8 sodium thiophenolate 
• 106820-14-8 2,3,4-Tri-O-acetyl-D-xylopyranose 
• 1233-03-0 α-D-xylopyranose tetraacetate 
• 28697-53-2 D-arabinopyranose 

Downstream Products

• 107961-12-6 β-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,4-tri-O-acetyl-D-arabinopyranose 
• 303153-45-9 4-azido-2-O-benzoyl-4,6-dideoxy-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-galactopyranosyl fluoride 
• 1007852-62-1 C₃₁H₃₃FO₁₃ 
• 1007855-12-0 2,4-di-O-benzoyl-6-deoxy-3-O-(2,3,4-tri-O-acetyl-α-D-xylopyranosyl)-α-D-galactopyranosyl fluoride 
• 1352718-30-9 C₁₁H₁₄O₄S 
• 1352718-31-0 C₃₂H₃₂O₄S 
• 1352717-86-2 2,3,4-tri-O-benzyl-β-L-arabinopyranosyl chloride 
• 1352718-46-7 methyl 2,3-di-O-methyl-4-O-(2,3,4-tri-O-benzyl-α-L-arabinopyranosyl)-α-D-glucopyranoside 
• 1352718-47-8 methyl 2,3-di-O-methyl-6-O-(2,3,4-tri-O-benzyl-α-L-arabinopyranosyl)-α-D-glucopyranoside 
• 18039-26-4 2,3,4-tri-O-benzyloxy-L-arabinopyranose 
• 131771-66-9 phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-xylopyranoside 
• 870096-05-2 (2S,3R,4S,5R)-3,4,5-trimethoxy-2-(phenylthio)tetrahydro-2H-pyran 

Relevant articles and documents

Chloromethyl Glycosides as Versatile Synthons to Prepare Glycosyloxymethyl-Prodrugs

This work investigates the addition of monosaccharides to marketed drugs to improve their pharmacokinetic properties for oral absorption. To this end, a set of chloromethyl glycoside synthons were developed to prepare a variety of glycosyloxymethyl-prodrugs derived from 5-fluorouracil, thioguanine, propofol and losartan. Drug release was studied in vitro using β-glucosidase confirming rapid conversion of the monosaccharide prodrugs to release the parent drug, formaldehyde and the monosaccharide. To showcase this prodrug approach, a glucosyloxymethyl conjugate of the tetrazole-containing drug losartan was used for in vivo experiments and showed complete release of the drug in a dog-model.

Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones to Prepare C-Aryl Glycals and Acyclic Vinyl Ethers

We demonstrate that readily available and bench-stable α-oxo-vinylsulfones are competent electrophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling reactions. The C-sulfone bond in the α-oxo-vinylsulfone motif is cleaved chemoselectively in these reactions, furnishing C-aryl glycals or acyclic vinyl ethers in high yields. These reactions proceed under mild conditions and tolerate a remarkable scope of heterocycles and functional groups. Preliminary mechanistic studies revealed the importance of an α-heteroatom in facilitating these transformations.

Dehydrative Thioglycosylation of 1-Hydroxyl Glycosides Catalyzed by In Situ-Generated AlI3

Thioglycosylation of 1-hydroxyl glycosides catalyzed by in situ-generated AlI3 from elemental aluminium and molecular iodine has been developed. This method provides an alternative route to access anomeric thioglycosides without the use of hazard Lewis acidic activators or per-modified activated thiol sources. The major advantages of this dehydrative procedure are environmental friendly, ease of operation, high anomeric diastereoselectivity, and mild reaction conditions.