5'-Deoxy-5'-fluoro-5'-(methylthio)adenosine

Base Information

• Chemical Name: 5'-Deoxy-5'-fluoro-5'-(methylthio)adenosine
• CAS No.: 119771-21-0
• Molecular Formula: C₁₁H₁₄FN₅O₃S
• Molecular Weight: 315.328
• DSSTox Substance ID: DTXSID10923110
• Wikidata: Q82897027
• Mol file: 119771-21-0.mol

Synonyms:5'-deoxy-5'-fluoro-5'-(methylthio)adenosine;5'-deoxy-5'-fluoro-5'-(methylthio)adenosine, (5S)-isomer;5'-DFMA

Chemical Property of 5'-Deoxy-5'-fluoro-5'-(methylthio)adenosine

Chemical Property:

• Boiling Point: 649.5°Cat760mmHg
• Flash Point: 346.6°C
• PSA: 144.61000
• Density: 1.92g/cm³
• LogP: 0.26750
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 315.08013866
• Heavy Atom Count: 21
• Complexity: 384

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CSC(C1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)O)F
• Isomeric SMILES: CS[C@H]([C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)O)F

Technology Process of 5'-Deoxy-5'-fluoro-5'-(methylthio)adenosine

There total 3 articles about 5'-Deoxy-5'-fluoro-5'-(methylthio)adenosine 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:

2',3'-Di-O-acetyl-5'-deoxy-5'-(methylthio)adenosine sulfoxide (119771-16-3) → 5'-Deoxy-5'-methylthioadenosine (2457-80-9) + 5'-Deoxy-5'-<(monofluoromethyl)thio>adenosine (118560-47-7) + 5'-Deoxy-5'-fluoro-5'-(methylthio)adenosine (119771-21-0)

Guidance literature:

With dimethylaminosulphur trifluoride; ammonia; Yield given. Multistep reaction. Yields of byproduct given; 1) CHCl₃, 55 deg C, 2.5-3 h, 2) MeOH, r.t., 2.5 h;

DOI:10.1021/jm00125a012

Reference yield:

2',3'-Di-O-acetyl-5'-deoxy-5'-(methylthio)adenosine (119771-17-4) → 5'-Deoxy-5'-fluoro-5'-(methylthio)adenosine (119771-21-0)

Guidance literature:

Multi-step reaction with 2 steps

1: (diethylamino)sulfur trifluoride / SbCl₃ / CH₂Cl₂ / 2 h / Ambient temperature

2: NH₃ / methanol

With diethylamino-sulfur trifluoride; ammonia; antimony(III) chloride; In methanol; dichloromethane;

DOI:10.1021/jo00067a009

Reference yield:

5’-deoxy-5’-methylsulfinyladenosine (3387-65-3) → 5'-Deoxy-5'-fluoro-5'-(methylthio)adenosine (119771-21-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / 4-(dimethylamino)pyridine, Et₃N / acetonitrile / 1 h

2: 1) (dimethylamino)sulfur trifluoride, 2) NH₃ / 1) CHCl₃, 55 deg C, 2.5-3 h, 2) MeOH, r.t., 2.5 h

With dmap; dimethylaminosulphur trifluoride; ammonia; triethylamine; In acetonitrile;

DOI:10.1021/jm00125a012

upstream raw materials:

2',3'-Di-O-acetyl-5'-deoxy-5'-(methylthio)adenosine sulfoxide

2',3'-Di-O-acetyl-5'-deoxy-5'-(methylthio)adenosine

5’-deoxy-5’-methylsulfinyladenosine