2'-C-Methyl-, 2',3',5'-tribenzoateuridine

Base Information

• Chemical Name: 2'-C-Methyl-, 2',3',5'-tribenzoateuridine
• CAS No.: 23643-36-9
• Molecular Formula: C31H26 N2 O9
• Molecular Weight: 570.555
• Mol file: 23643-36-9.mol

Synonyms:Uridine,2'-C-methyl-, 2',3',5'-tribenzoate (8CI)

Chemical Property of 2'-C-Methyl-, 2',3',5'-tribenzoateuridine

Chemical Property:

• Melting Point: 201-202 °C
• PKA: 9.39±0.10(Predicted)
• PSA: 142.99000
• Density: 1.42±0.1 g/cm3(Predicted)
• LogP: 3.13230

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2'-C-Methyl-, 2',3',5'-tribenzoateuridine

There total 19 articles about 2'-C-Methyl-, 2',3',5'-tribenzoateuridine 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: 90.3%

uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) + 1,2,3,5-tetra-O-benzoyl-2-C-methyl-β-D-ribofuranose (15397-15-6) → 2′,3′,5′-tri-O-benzoyl-2′-C-methyluridine (23643-36-9)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; tin(IV) chloride; In acetonitrile; at 75 ℃; Temperature;

Reference yield: 90.0%

uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) + (2S/R,3R,4R,5R)-5-((benzoyloxy)methyl)-3-methyltetrahydrofuran-2,3,4-triyltribenzoate → 2′,3′,5′-tri-O-benzoyl-2′-C-methyluridine (23643-36-9)

Guidance literature:

uracil; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; at 80 ℃; for 1h;

(2S/R,3R,4R,5R)-5-((benzoyloxy)methyl)-3-methyltetrahydrofuran-2,3,4-triyltribenzoate; With tin(IV) chloride; In acetonitrile; for 3h; Reflux;

DOI:10.1039/c5ob00427f

Reference yield: 75.0%

uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) + 1,2,3,5-tetra-O-benzoyl-2-C-methyl-β-D-ribofuranose (15397-15-6) → C31H26N2O9 + 2′,3′,5′-tri-O-benzoyl-2′-C-methyluridine (23643-36-9)

Guidance literature:

uracil; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; at 20 ℃; for 0.333333h;

1,2,3,5-tetra-O-benzoyl-2-C-methyl-β-D-ribofuranose; With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at -20 - 70 ℃; for 2h; Overall yield = 983 mg;

DOI:10.1016/j.bmc.2015.07.003

upstream raw materials:

uracil

1,2,3,5-tetra-O-benzoyl-2-C-methyl-β-D-ribofuranose

1,2,3,5-Tetra-O-benzoyl-2-C-methyl-α(β)-D-ribofuranose

1,3-bis(trimethylsilyl)uracil

Downstream raw materials:

3'-O-[N-(tert-butoxycarbonyl)-L-valinyl]-2'-C-methyl-β-D-cytidine

2'-C-methylcytidine

5-bromo-1-(2'-methyl-2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-1H-pyrimidine-2,4-dione

C₂₄H₂₀N₂O₇

Refernces

• 1、 Wang, Gang,Lim, Siew Pheng,Chen, Yen-Liang,Hunziker, Jürg,Rao, Ranga,Gu, Feng,Seh, Cheah Chen,Ghafar, Nahdiyah Abdul,Xu, Haoying,Chan, Katherine,Lin, Xiaodong,Saunders, Oliver L.,Fenaux, Martijn,Zhong, Weidong,Shi, Pei-Yong,Yokokawa, Fumiaki. "Structure-activity relationship of uridine-based nucleoside phosphoramidate prodrugs for inhibition of dengue virus RNA-dependent RNA polymerase". . p. 2324 - 2327. Retrieved 2018/05/28.
• 2、 Maiti, Munmun,Maiti, Mohitosh,Rozenski, Jef,De Jonghe, Steven,Herdewijn, Piet. "Aspartic acid based nucleoside phosphoramidate prodrugs as potent inhibitors of hepatitis C virus replication". . p. 5158 - 5174. Retrieved 2015/05/13.