2-fluoro-2',3'-dideoxyadenosine

Base Information

• Chemical Name: 2-fluoro-2',3'-dideoxyadenosine
• CAS No.: 114849-59-1
• Molecular Formula: C10H12 F N5 O2
• Molecular Weight: 253.236
• Mol file: 114849-59-1.mol

Synonyms:18: PN:WO03035012 PAGE: 53 claimed sequence; 2-Fluoro-2',3'-dideoxyadenosine

Chemical Property of 2-fluoro-2',3'-dideoxyadenosine

Chemical Property:

• Boiling Point: 603.6oC at 760 mmHg
• Flash Point: 318.9oC
• PSA: 99.08000
• Density: 1.85g/cm3
• LogP: 0.79870

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-fluoro-2',3'-dideoxyadenosine

There total 1 articles about 2-fluoro-2',3'-dideoxyadenosine 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:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → 6-Amino-2-fluoro-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)purine (114849-59-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 98 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

2: 1) lithium hexamethyldisilazide / 1) THF, -78 deg C, 1h, 2) room temperature, 30 min

3: tetrahydrofuran / -78 °C

4: DIBAL-H / toluene / 2 h / -78 °C

5: 96 percent / pyridine, DMAP / CH₂Cl₂ / 2 h / 0 °C

6: 1) hexamethyldisilazane (HMDS), ammonium sulfate, 2) trimethylsilyl triflate (TMSOTf) / 1) reflux, 3 h, 2) 1,2-dichloroethane, -25 deg C, 30 min

7: 52 percent / ammonia (g) / 1,2-dimethoxy-ethane / 18 h

8: 94.7 percent / n-Bu₃SnH, Et₃B / benzene; hexane / Ambient temperature

9: 79 percent / TBAF / tetrahydrofuran / Ambient temperature

With pyridine; 1H-imidazole; dmap; ammonium sulfate; triethyl borane; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; ammonia; tri-n-butyl-tin hydride; diisobutylaluminium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; lithium hexamethyldisilazane; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/jo00040a031

Reference yield: 10.0%

Dimethyldisulphide (624-92-0) + 6-Amino-2-fluoro-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)purine (114849-59-1) → 2',3'-Dideoxy-2-(methylthio)adenosine (122970-32-5)

Guidance literature:

Dimethyldisulphide; With sodium; In tetrahydrofuran; acetonitrile; Heating;

6-Amino-2-fluoro-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)purine; In tetrahydrofuran; acetonitrile; at 20 ℃; for 0.5h;

upstream raw materials:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

Downstream raw materials:

2',3'-Dideoxy-2-(methylthio)adenosine