2'-C-Methyluridine

Base Information

• Chemical Name: 2'-C-Methyluridine
• CAS No.: 31448-54-1
• Molecular Formula: C10H14 N2 O6
• Molecular Weight: 258.231
• Mol file: 31448-54-1.mol

Synonyms:2'-C-Methyluridine

Chemical Property of 2'-C-Methyluridine

Chemical Property:

• Melting Point: 110-112 ºC
• PKA: 9.39±0.10(Predicted)
• PSA: 124.78000
• Density: 1.572
• LogP: -2.46180
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

2''-C-Methyluridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A 2’C-Me branched C-nucleoside that shows HCV polymerase inhibitory activity. A 2’-C-Me branched C-nucleoside that shows HCV polymerase inhibitory activity.

Technology Process of 2'-C-Methyluridine

There total 2 articles about 2'-C-Methyluridine 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: 100.0%

2′,3′,5′-tri-O-benzoyl-2′-C-methyluridine (23643-36-9) → 2'-C-methyluridine (31448-54-1)

Guidance literature:

With ammonia; In methanol; at 0 - 4 ℃; for 48h;

DOI:10.1021/jo034263y

Reference yield:

1,3,5-tri-O-benzoyl-α-D-ribofuranoside (22224-41-5) → 2'-C-methyluridine (31448-54-1)

Guidance literature:

Multi-step reaction with 3 steps

1: Dess-Martin periodane, MgSO₄ / CH₂Cl₂

2: TiCl₄, dimethylaminopyridine, Et₃N

3: 1.) (TMSO)(TMSN)C(Me), SnCl₄; 2.) NH₃ / 1.) acetonitrile, reflux, 3 h; 2.) MeOH

With dmap; N,O-bis-(trimethylsilyl)-acetamide; ammonia; titanium tetrachloride; tin(IV) chloride; magnesium sulfate; Dess-Martin periodane; triethylamine; In dichloromethane;

DOI:10.1016/0040-4039(95)01635-U

Reference yield: 93.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2'-C-methyluridine (31448-54-1) → 5'-O-(4,4-dimethoxytrityl)-2'-C-methyluridine (1158728-87-0)

Guidance literature:

With dmap; triethylamine; In ethyl acetate; at 50 ℃; for 3h;

upstream raw materials:

2′,3′,5′-tri-O-benzoyl-2′-C-methyluridine

1,3,5-tri-O-benzoyl-α-D-ribofuranoside

Downstream raw materials:

3'-deoxy-2'-C-methyluridine

2'-deoxy-2'-C-β-methyl-N⁴-benzoylcytidine

3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-2'-C-β-methyl-N⁴-benzoylcytidine

5'-O-(dimethoxytrityl)-2'-deoxy-2'-C-β-methyl-N⁴-benzoylcytidine

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.