Uridine, 5'-O-(triphenylmethyl)-, 2',3'-dimethanesulfonate

Base Information

• Chemical Name: Uridine, 5'-O-(triphenylmethyl)-, 2',3'-dimethanesulfonate
• CAS No.: 110524-37-3
• Molecular Formula: C30H30N2O10S2
• Molecular Weight: 642.708
• Mol file: 110524-37-3.mol

Synonyms:Uridine, 5'-O-(triphenylmethyl)-, 2',3'-dimethanesulfonate

Chemical Property of Uridine, 5'-O-(triphenylmethyl)-, 2',3'-dimethanesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Uridine, 5'-O-(triphenylmethyl)-, 2',3'-dimethanesulfonate

There total 6 articles about Uridine, 5'-O-(triphenylmethyl)-, 2',3'-dimethanesulfonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.2%

methanesulfonyl chloride (124-63-0) + 5'-O-trityluridine (6554-10-5) → 1-[2,3-di-O-(metanesulfonyl)-5-O-(triphenylmethyl)-β-D-ribofuranosyl]pyrimidine-2,4(1H,3H)-dione (110524-37-3)

Guidance literature:

With pyridine; at 0 ℃;

DOI:10.1016/j.tet.2010.12.054

Reference yield:

uridine (58-96-8) → 1-[2,3-di-O-(metanesulfonyl)-5-O-(triphenylmethyl)-β-D-ribofuranosyl]pyrimidine-2,4(1H,3H)-dione (110524-37-3)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 2 h / 100 °C

2: 15 h / 4 °C

With pyridine;

DOI:10.1039/b002155p

Reference yield:

trityl chloride (76-83-5) → 1-[2,3-di-O-(metanesulfonyl)-5-O-(triphenylmethyl)-β-D-ribofuranosyl]pyrimidine-2,4(1H,3H)-dione (110524-37-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / pyridine / 1.25 h / 70 - 85 °C

2: Et₃N / tetrahydrofuran / 1.25 h / -5 - 5 °C

With pyridine; triethylamine; In tetrahydrofuran;

DOI:10.1016/S0040-4020(97)00500-0

upstream raw materials:

methanesulfonyl chloride

5'-O-trityluridine

trityl chloride

uridine

Downstream raw materials:

(2R,3S,4R,5S)-4-azido-2-(2,4-dioxo-3,4-dihydropyrimidine-1(2H)-yl)-5-(trityloxymethyl)-tetrahydrofuran-3-ylacetate

1-[3-azido-3-deoxy-5-O-(triphenylmethyl)-β-D-arabinofuranosyl]pyrimidine-2,4-(1H,3H)-dione

1-[(2R,3S,4R,5R)-5-Hydroxymethyl-3-((R)-2-oxo-cyclohexyl)-4-(toluene-4-sulfonyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

1-[(2R,3S,4R,5R)-5-Hydroxymethyl-3-((S)-2-oxo-cyclohexyl)-4-(toluene-4-sulfonyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Refernces

• 1、 Shakya, Neeraj,Srivastav, Naveen C.,Desroches, Nancy,Agrawal, Babita,Kunimoto, Dennis Y.,Kumar, Rakesh. "3′-Bromo analogues of pyrimidine nucleosides as a new class of potent inhibitors of mycobacterium tuberculosis". experimental part. p. 4130 - 4140. Retrieved 2010/09/04.
• 2、 Faul, Margaret M.,Huff, Bret E.,Dunlap, Steven E.,Frank, Scott A.,Fritz, James E.,Kaldor, Stephen W.,LeTourneau, Michael E.,Staszak, Michael A.,Ward, Jeffrey A.,Werner, John A.,Winneroski, Leonard L.. "Synthesis of 2',3'-dideoxy-3'-hydroxymethylcytidine; A unique antiviral nucleoside". . p. 8085 - 8104. Retrieved 2007/10/03.