52544-88-4

Basic information

• Product Name: phenyl 2,3,5-tri-O-acetyl-1-thio-β-D-ribofuranoside
• Synonyms: phenyl 2,3,5-tri-O-acetyl-1-thio-β-D-ribofuranoside
• CAS NO: 52544-88-4
• Molecular Weight: 368.408
• Mol File: 52544-88-4.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: phenyl 2,3,5-tri-O-acetyl-1-thio-β-D-ribofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 2,3,5-tri-O-acetyl-1-thio-β-D-ribofuranoside(52544-88-4)
• EPA Substance Registry System: phenyl 2,3,5-tri-O-acetyl-1-thio-β-D-ribofuranoside(52544-88-4)

Safety Data

• Hazardous Substances Data: 52544-88-4(Hazardous Substances Data)

Upstream product

• 4551-15-9 phenylthiotrimethylsilane 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 28708-32-9 1,2,3,5-tetra-O-acetyl-D-ribofuranose 
• 930-69-8 sodium thiophenolate 
• 1107622-21-8 2,3,5-tri-O-acetyl-1-thio-β-D-ribofuranose 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 1199614-81-7 2,3,5-tri-O-acetyl-D-ribofuranose 
• 108-98-5 thiophenol 

Downstream Products

• 942420-67-9 5-O-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6,3',4'-tri-O-acetyl-1,3,2',6'-tetraazidoneamine 
• 107961-31-9 methyl 2-(phenylsulfinyl)-2-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-acetate 
• 107961-30-8 methyl 2-(phenylthio)-2-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-acetate 
• 153362-34-6 β-phenylthio-2,3-O-isopropylidene-D-ribofuranose 
• 153362-33-5 Diazo-acetic acid (3aR,4R,6S,6aR)-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 
• 262421-85-2 (2S,3R,3aS,9aR)-5,5,7,7-Tetraisopropyl-2-phenylsulfanyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-ol 
• 64691-28-7 Phenyl 1-thio-β-D-ribofuranoside 
• 107961-13-7 β-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,5-tri-O-acetyl-D-ribofuranose 
• 942420-69-1 5-O-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1-N-[(S)-4-(benzyloxycarbonylamino)-2-hydroxybutanoyl]-6,3',4'-tri-O-acetyl-3,2',6'-triazidoneamine 
• 942420-68-0 5-O-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1-N-tert-butoxycarbonyl-6,3',4'-tri-O-acetyl-3,2',6'-triazidoneamine 

Relevant articles and documents

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.

Transition-metal-free synthesis of aryl 1-thioglycosides with arynes at room temperature

A mild, convenient and transition-metal-free protocol for the synthesis of aryl 1-thioglycosides is presentedviaarynes generatedin situcombined with glycosyl thiols in the presence of TBAF(tBuOH)4. The methodology provides a general and efficient way to prepare a series of functionalized thioglycosides in good to excellent yields with a perfect control of the anomeric configuration at room temperature. In addition, the reaction conditions tolerate a variety of the pentoses and hexoses, and the reaction also performs smoothly on protected monosaccharides and disaccharides.

Highly diastereoselective thioglycosylation of functionalized peracetylated glycosides catalyzed by MoO2Cl2

Among 18 oxometallic species, MoO2Cl2 was found to be the most reactive in catalytic thioglycosylation of O-acetylated glycosides with functionalized thiols in CH2Cl2, leading cleanly to 1,2-trans-thioglycosides with exclusive diastereocontrol. The new catalytic protocol is applicable to a monoglycoside building block and β-(1→6)-S-linked-thiodisaccharide synthesis.