115913-84-3

Basic information

• Product Name: 1-(2,3-anhydro-5-O-trityl-beta-D-glycero-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione
• Synonyms: 2,4(1H,3H)-Pyrimidinedione, 1-[2,3-anhydro-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]-5-methyl-
• CAS NO: 115913-84-3
• Molecular Formula: C₂₉H₂₆N₂O₅
• Molecular Weight: 482.5271
• Mol File: 115913-84-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 174-175 °C
• Density: 1.294g/cm³
• Refractive Index: 1.624
• PKA: 9.44±0.10(Predicted)
• CAS DataBase Reference: 1-(2,3-anhydro-5-O-trityl-beta-D-glycero-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,3-anhydro-5-O-trityl-beta-D-glycero-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione(115913-84-3)
• EPA Substance Registry System: 1-(2,3-anhydro-5-O-trityl-beta-D-glycero-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione(115913-84-3)

Safety Data

• Hazardous Substances Data: 115913-84-3(Hazardous Substances Data)

Upstream product

• 124493-84-1 5-methyl-5'-O-(triphenylmethyl)uridine 2',3'-bis(methanesulfonate) 
• 159407-15-5 (5S,6S)-2,2'-anhydro-5-bromo-1-(3'-bromo-3'-deoxy-5'-O-trityl-β-D-arabinofuranosyl)-6-methoxy-5,6-dihydrothymine 
• 159353-49-8 (5R,6R)-2,2'-anhydro-5-bromo-1-(3'-bromo-3'-deoxy-5'-O-trityl-β-D-arabinofuranosyl)-6-methoxy-5,6-dihydrothymine 
• 5964-41-0 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl-5-O-trityl)thymine 
• 145919-54-6 2,2'-anhydro-1-(3'-deoxy-3'-bromo-5'-O-trityl-β-D-arabinofuranosyl)-(5S,6S)-trans-5-bromo-6-hydroxy-5,6-dihydrothymine 
• 145819-51-8 2,2'-anhydro-1-(3'-deoxy-3'-bromo-5'-O-trityl-β-D-arabinofuranosyl)-(5R,6R)-trans-5-bromo-6-hydroxy-5,6-dihydrothymine 
• 145919-55-7 (5R,6S)-2,2'-anhydro-1-(3'-bromo-3'-deoxy-5'-O-trityl-β-D-arabinofuranosyl)-5,6-epoxy-5,6-dihydrothymine 
• 145819-52-9 (5S,6R)-2,2'-anhydro-1-(3'-bromo-3'-deoxy-5'-O-trityl-β-D-arabinofuranosyl)-5,6-epoxy-5,6-dihydrothymine 
• 1463-10-1 5-Methyluridine 
• 101796-28-5 1-(5'-O-trityl-β-D-ribofuranosyl)thymine 
• 142545-13-9 1-(2,3-anhydro-5-O-trityl-β-D-lyxofuranosyl)-2-O-methylthymine 
• 145819-53-0 2,2'-anhydro-1-(3'-deoxy-3'-bromo-5'-O-trityl-β-D-arabinofuranosyl)thymine 

Downstream Products

• 130351-53-0 1-[(2R,3S,4S,5S)-3-Hydroxy-4-(5-methyl-[1,3,5]dithiazinan-2-yl)-5-trityloxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 774226-07-2 1-(3-deoxy-3-phenylseleno-5-O-trityl-β-D-arabinofuranosyl)thymine 
• 1227358-38-4 1-(3-bromo-3-deoxy-5-O-trityl-β-D-arabinofuranosyl)thymine 
• 1227358-41-9 1-(2-bromo-2-deoxy-5-O-trityl-β-D-xylofuranosyl)thymine 
• 124355-34-6 1-<3-(1,2,4-triazol-1-yl)-3-deoxy-β-D-arabinofuranosyl>thymine 
• 124355-31-3 1-(3-imidazol-1-yl-3-deoxy-β-D-arabinofuranosyl)thymine 
• 124379-59-5 1-(3-pyrazol-1-yl-3-deoxy-β-D-arabinofuranosyl)thymine 
• 129678-64-4 1-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-C-(4,5-dihydro-5-methyl-1,3,5-dithiazin-2-yl)-β-D-arabino-pentofuranosyl>thymine 
• 129678-53-1 1-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-C-formyl-β-D-arabino-pentofuranosyl>thymine 
• 129707-48-8 1-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-C-(hydroxymethyl)-β-D-arabino-pentofuranosyl>thymine 
• 130468-30-3 1-<3-deoxy-3-C-(4,5-dihydro-5-methyl-1,3,5-dithiazin-2-yl)-β-D-arabino-pentofuranosyl>thymine 
• 130351-55-2 1-<3-deoxy-3-C-(hydroxymethyl)-β-D-arabino-pentofuranosyl>thymine 
• 130351-67-6 1-(3-deoxy-3-C-formyl-β-D-lyxo-pentofuranosyl)thymine 3',5'-O-hemiacetal 
• 132776-25-1 1-(3-azido-2,3-dideoxy-2-fluoro-5-O-trityl-β-D-ribofuranosyl)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.

Highly Efficient Synthesis of 2,2'-Anhydro-1-(3'-bromo-3'-deoxy-5'-O-trityl-β-D-arabinofuranosyl)thymine and its Derivatives from an Unsaturated Thymine Nucleoside

Reaction of 5'-O-trityl-2',3'-thymidinene 1 with hypobromous acid gave (5R,6R)-2,2'-anhydro-5-bromo-1-(3'-bromo-3'-deoxy-5'-O-trityl-β-D-arabinofuranosyl)-6-hydroxy-5,6-dihydrothymine 3a and its (5S,6S)-trans isomer 4a.Similarly, 6-methoxy analogues (3b a

Fluorinated sugar analogues of potential anti-HIV-1 nucleosides

In order to obtain agents with therapeutic indices superior to those of AZT, FLT, or D4T, several analogues of anti-HIV-1 nucleosides were synthesized. These include 2',3'-dideoxy-2',3'-difluoro-5-methyluridine (13), its arabino analogue 19, arabino-5-met