124493-84-1

Basic information

• Product Name: Uridine,5-methyl-5'-O-(triphenylmethyl)-, 2',3'-dimethanesulfonate (9CI)
• CAS NO: 124493-84-1
• Molecular Formula: C31H32 N2 O10 S2
• Molecular Weight: 656.734
• Mol File: 124493-84-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Uridine,5-methyl-5'-O-(triphenylmethyl)-, 2',3'-dimethanesulfonate (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Uridine,5-methyl-5'-O-(triphenylmethyl)-, 2',3'-dimethanesulfonate (9CI)(124493-84-1)
• EPA Substance Registry System: Uridine,5-methyl-5'-O-(triphenylmethyl)-, 2',3'-dimethanesulfonate (9CI)(124493-84-1)

Safety Data

• Hazardous Substances Data: 124493-84-1(Hazardous Substances Data)

Upstream product

• 76-83-5 trityl chloride 
• 124-63-0 methanesulfonyl chloride 
• 1463-10-1 5-Methyluridine 
• 101796-28-5 1-(5'-O-trityl-β-D-ribofuranosyl)thymine 

Downstream Products

• 132776-25-1 1-(3-azido-2,3-dideoxy-2-fluoro-5-O-trityl-β-D-ribofuranosyl)thymine 
• 128269-50-1 1-(3-azido-3-deoxy-5-O-trityl-β-D-arabinofuranosyl)thymine 
• 132776-24-0 1-(2-azido-2-deoxy-5-O-trityl-β-D-xylofuranosyl)thymine 
• 132776-26-2 2'-azido-2',3'-dideoxy-3'-fluoro-5'-O-trityl-5-methyluridine 
• 128114-97-6 1-(3-deoxy-2-fluoro-5-O-trityl-β-D-arabinofuranosyl)thymine 
• 774226-09-4 1-[2-O-acetyl-5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-phenylseleno-β-D-arabinofuranosyl]thymine 
• 180699-58-5 1-[5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-phenylseleno-β-D-arabinofuranosyl]thymine 
• 774226-07-2 1-(3-deoxy-3-phenylseleno-5-O-trityl-β-D-arabinofuranosyl)thymine 
• 774226-10-7 1-[2-O-acetyl-5-O-(tert-butyldiphenylsilyl)-β-D-glycero-pent-3-enofuranosyl]thymine 
• 774226-11-8 5'-O-(tert-butyldiphenylsilyl)-4'-cyano-2',3'-didehydro-3'-deoxythymidine 
• 774226-13-0 1-(3-deoxy-3-phenylseleno-β-D-arabinofuranosyl)thymine 
• 5964-41-0 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl-5-O-trityl)thymine 
• 115913-84-3 1-(2,3-epoxy-5-O-trityl-β-D-lyxo-pentofuranosyl)thymine 

Relevant articles and documents

3′-Bromo analogues of pyrimidine nucleosides as a new class of potent inhibitors of mycobacterium tuberculosis

Tuberculosis (TB) is a major health problem worldwide. We herein report a new class of pyrimidine nucleosides as potent inhibitors of Mycobacterium tuberculosis (M. tuberculosis). Various 2′- or 3′-halogeno derivatives of pyrimidine nucleosides containing uracil, 5-fluorouracil, and thymine bases were synthesized and evaluated for antimycobacterial activities. Among the compounds tested, 3′-bromo-3′-deoxy- arabinofuranosylthymine (33) was the most effective antituberculosis agent in the in vitro assays against wild-type M. tuberculosis strain (H37Ra) (MIC 50 = 1 μg/mL) as well as drug-resistant (H37Rv) (rifampicin-resistant and isoniazid-resistant) strains of M. tuberculosis (MIC50 = 1-2 μg/mL). Compound 33 also inhibited intracellular M. tuberculosis in a human monocytic cell line infected with H37Ra, demonstrating higher activity against intramacrophagic mycobacteria (80% reduction at 10 μg/mL concentration) than extracellular mycobacteria (75% reduction at 10 μg/mL concentration). In contrast, pyrimidine nucleosides possessing 5-fluorouracil base were weak inhibitors of M. tuberculosis. No cytotoxicity was found up to the highest concentration of compounds tested (CC50 > 100-200 μg/mL) against a human cell line. Overall, these encouraging results substantiate the potential of this new class of compounds as promising antituberculosis agents.

1-(3'-fluoro-2',3'-dideoxy-β-D-ribofuranosyl)-5-substituted pyrimidine nucleosides

A 2',3'-deoxy-3'-fluoro-pyrimidine nucleoside having the formula: STR1 wherein R1 is OH or NH2 ; R2 is CF3, CH2 CH2 CH3, STR2 CH2 OCH3, CH2 SCH3, CH=CH2 CH=CH--CH3, C CH, C C--CH3 or CH2 --C CH; or a pharmaceutically acceptable salt thereof. These nucleoside analogs exhibit antiviral activity against HIV.

Deoxygenation of cis vicinal diols to make didehydro dideoxy nucleosidies and synthetic intermediates

Cis vicinal diols are converted to olefins using tellurides or selenide reagents. The diol is reacted to convert the hydroxyl groups into good leaving groups for nucleophilic substitution. Alkyl and aryl sulfonate groups such as mesylate or tosylate are p