52544-88-4

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 
• 108-98-5 thiophenol 
• 1199614-81-7 2,3,5-tri-O-acetyl-D-ribofuranose 
• 1107622-21-8 2,3,5-tri-O-acetyl-1-thio-β-D-ribofuranose 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 930-69-8 sodium thiophenolate 

Downstream Products

• 64691-28-7 Phenyl 1-thio-β-D-ribofuranoside 
• 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 
• 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 
• 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 
• 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 
• 153362-34-6 β-phenylthio-2,3-O-isopropylidene-D-ribofuranose 
• 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 
• 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 
• 107961-13-7 β-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,5-tri-O-acetyl-D-ribofuranose 

Relevant academic research and scientific papers

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.

Concise Synthesis of 1-Thioalkyl Glycoside Donors by Reaction of Per-O-acetylated Sugars with Sodium Alkanethiolates under Solvent-Free Conditions

A relatively green method for synthesizing 1-thioalkyl glycosides has been developed, where sodium alkanethiolates were used to react with per-O-acetylated sugars instead of odorous alkyl mercaptans in the presence of BF3·Et2O without the use of solvents under mild conditions. Furthermore, we found that 1,2-trans-β-thioglycosides can be converted into corresponding 1,2-cis-α-thioglycosides in the presence of trifluoromethanesulfonic acid in nonpolar solvents under mild conditions. This provides a simple and efficient new approach for synthesizing challenging 1,2-cis-α-thioglycosides.

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.

Diastereoselective thioglycosylation of peracetylated glycosides catalyzed by in situ generated iron(III) iodide from elemental iodine and iron

A facile in situ preparation of Fe(III) iodide from cheap, abundant elemental iodine and iron metal served as an efficient catalyst for the thioglycosylation of peracetylated glycosides with various alkyl and aryl mercaptans. Due to neighboring participation, the anomerically pure β-thioglycosides were obtained in good to high yields with exclusive diastereocontrol.

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.

Antimicrobial 2-deoxystreptamine compounds

The present invention is directed to analogs of aminoglycoside compounds of the class having a glycosylated 2-deoxystreptamine (2-DOS) ring as well as their preparation and use as prophylactic or therapeutics against microbial infection. Compounds of the

Stereoselective synthesis of nucleosides from 1-thio and 1-seleno glycosides through consecutive 1,2-migration and glycosylation under Mitsunobu conditions

2-Deoxy-2-sulfenyl-arabino-α-nucleosides and 2-deoxy-2-sulfenyl-ribo- β-nucleosides were obtained with excellent stereoselectivity from 1-thio- ribo- and 1-thio-arabino-glycosides under Mitsunobu conditions.

A novel route to a new lactone intermediate for C-nucleosides via an intramolecular sulfonium ylide rearrangement. A formal synthesis of (+)-showdomycin

The lactone of 3,6-anhydro-4,5-O-isopropylidene-2-thiophenoxy-D-allo-heptonic acid was prepared by means of an intramolecular carbenoid-phenylthiofuranose reaction.