2-Thiocytidine

Base Information

• Chemical Name: 2-Thiocytidine
• CAS No.: 13239-97-9
• Molecular Formula: C₉H₁₃N₃O₄S
• Molecular Weight: 259.286
• European Community (EC) Number: 236-214-8
• DSSTox Substance ID: DTXSID30157516
• Nikkaji Number: J213.771B
• Wikidata: Q20890505
• Metabolomics Workbench ID: 53724
• Mol file: 13239-97-9.mol

Synonyms:2-thiocytidine

Chemical Property of 2-Thiocytidine

Chemical Property:

• Vapor Pressure: 6.17E-14mmHg at 25°C
• Melting Point: 208-209 °C
• Refractive Index: 1.788
• Boiling Point: 540.5 °C at 760 mmHg
• PKA: 12.97±0.70(Predicted)
• Flash Point: 280.7 °C
• PSA: 145.85000
• Density: 1.85 g/cm³
• LogP: -0.61250
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 259.06267708
• Heavy Atom Count: 17
• Complexity: 386

Purity/Quality:

99% ^*data from raw suppliers

2-Thiocytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN(C(=S)N=C1N)C2C(C(C(O2)CO)O)O
• Isomeric SMILES: C1=CN(C(=S)N=C1N)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
• Uses: 2-Thiocytidine (CAS# 13239-97-9) is a cytidine analogue. A profiled metabolite in HFD-induced obese mice after oral administration of Huangjinya green tea extract.

Technology Process of 2-Thiocytidine

There total 5 articles about 2-Thiocytidine 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: 76.0%

α-2-thioribocytidine → 2-thiocytidine (13233-20-0,13239-97-9) + 1-α-D-ribofuranosylcytosine (13913-16-1)

Guidance literature:

With water; for 60h; UV-irradiation;

DOI:10.1038/nchem.2664

Reference yield: 56.0%

4-methylsulfanyl-1-(β-D-ribofuranosyl)pyrimidine-2(1H)-thione (25030-30-2) → 2-thiocytidine (13233-20-0,13239-97-9)

Guidance literature:

With ammonia; In methanol; at 50 ℃; for 24h;

DOI:10.1002/ejoc.200500556

Reference yield:

1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-methylsulfanyl-1,2-dihydropyrimidin-2-thione (627812-08-2) → 2-thiocytidine (13233-20-0,13239-97-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / K₂CO₃ / methanol; CH₂Cl₂ / 7 h / 0 °C

2: 56 percent / NH₃ / methanol / 24 h / 50 °C

With ammonia; potassium carbonate; In methanol; dichloromethane;

DOI:10.1002/ejoc.200500556

upstream raw materials:

4-methylsulfanyl-1-(β-D-ribofuranosyl)pyrimidine-2(1H)-thione

1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-methylsulfanyl-1,2-dihydropyrimidin-2-thione

Downstream raw materials:

2,4-diaminopyrimidine

cytidine 2′,3′-cyclic monophosphate

CYTIDINE

2-thiouridine

Refernces

• 1、 Xu, Jianfeng,Tsanakopoulou, Maria,Magnani, Christopher J.,Szabla, Rafa?,?poner, Judit E.,?poner, Ji?í,Góra, Robert W.,Sutherland, John D.. "A prebiotically plausible synthesis of pyrimidine β-ribonucleosides and their phosphate derivatives involving photoanomerization". . p. 303 - 309. Retrieved 2017/04/03.
• 2、 Russell,Prystasz,Hamamura,Verheyden,Moffatt. "Reactions of 2 acyloxyisobutyryl haloides with nucleosides. V. Reactions with cytidine and its derivatives". . p. 2182 - 2186. Retrieved 2007/10/04.