2'-Methyl-2'-deoxyidenecytidine

Base Information

• Chemical Name: 2'-Methyl-2'-deoxyidenecytidine
• CAS No.: 119804-96-5
• Molecular Formula: C10H13 N3 O4
• Molecular Weight: 239.231
• DSSTox Substance ID: DTXSID60923120
• ChEMBL ID: CHEMBL234442
• Mol file: 119804-96-5.mol

Synonyms:119804-96-5;SCHEMBL18266;CHEMBL234442;DTXSID60923120;1-(2-Deoxy-2-methylidenepentofuranosyl)-4-imino-1,4-dihydropyrimidin-2-ol

Chemical Property of 2'-Methyl-2'-deoxyidenecytidine

Chemical Property:

• Melting Point: 190-194 °C (decomp)(Solv: water (7732-18-5))
• Boiling Point: 494.8°Cat760mmHg
• PKA: 13.29±0.60(Predicted)
• Flash Point: 253.1°C
• PSA: 110.60000
• Density: 1.63g/cm³
• LogP: -0.78650
• XLogP3: -2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 239.09060590
• Heavy Atom Count: 17
• Complexity: 418

Purity/Quality:

97% ^*data from raw suppliers

DMDC 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C1C(C(OC1N2C=CC(=NC2=O)N)CO)O
• Isomeric SMILES: C=C1[C@@H](O[C@@H](C1O)CO)N2C=CC(=NC2=O)N

Technology Process of 2'-Methyl-2'-deoxyidenecytidine

There total 11 articles about 2'-Methyl-2'-deoxyidenecytidine 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: 92.0%

3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-2'-methylidenecytidine (130954-04-0) → 2'-deoxy-2'-methylenecytidine (119804-96-5)

Guidance literature:

With n-Bu₄F; In tetrahydrofuran; for 1.5h; Ambient temperature;

DOI:10.1021/jm00112a040

Reference yield: 83.0%

→ 2'-deoxy-2'-methylenecytidine (119804-96-5)

Guidance literature:

Reference yield: 81.0%

4-ethoxy-(2-deoxy-2'-methylidene-β-D-ribofuranosyl)-2-(1H)-pyrimidinone (113648-24-1) → 2'-deoxy-2'-methylenecytidine (119804-96-5)

Guidance literature:

With ammonia; In methanol; at 100 ℃; for 48h;

DOI:10.1021/jm00401a001

upstream raw materials:

4-ethoxy-(2-deoxy-2'-methylidene-β-D-ribofuranosyl)-2-(1H)-pyrimidinone

3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-2'-methylidenecytidine

3',5'-bis-O-tert-butyldimethylsilyl-2'-deoxy-2'-methylidenecytidine

N⁴-benzoyl-1-[2-deoxy-2-methylidene-3,5-di-O-benzoyl-β-D-glycero-pentofuranosyl]cytosine

Downstream raw materials:

1-(2-deoxy-2-methylene-β-D-erythro-pentofuranosyl)-4-N-[γ-[α-[2-(trimethylsilyl)ethoxy]-2-N-[2-(trimethylsilyl)ethoxycarbonyl]folyl]]cytosine

Refernces

• 1、 Clark, Jeremy L.,Hollecker, Laurent,Mason, J. Christian,Stuyver, Lieven J.,Tharnish, Phillip M.,Lostia, Stefania,McBrayer, Tamara R.,Schinazi, Raymond F.,Watanabe, Kyoichi A.,Otto, Michael J.,Furman, Phillip A.,Stec, Wojciech J.,Patterson, Steven E.,Pankiewicz, Krzysztof W.. "Design, synthesis, and antiviral activity of 2′-deoxy-2′- fluoro-2′-C-methylcytidine, a potent inhibitor of hepatitis C virus replication". . p. 5504 - 5508. Retrieved 2007/10/03.
• 2、 Samano,Robins. "Stereoselective addition of a Wittig reagent to give a single nucleoside oxaphosphetane diastereoisomer. Synthesis of 2'(and 3')-deoxy-2'(and 3')-methyleneuridine (and cytidine) derivatives from uridine ketonucleosides". . p. 283 - 288. Retrieved 2007/10/02.