2-(2-amino-6-chloro-9H-purin-9-yl)-1,4-anhydro-2,3-dideoxy-1-thio-L-threo-pentitol

Base Information

• Chemical Name: 2-(2-amino-6-chloro-9H-purin-9-yl)-1,4-anhydro-2,3-dideoxy-1-thio-L-threo-pentitol
• CAS No.: 142941-60-4
• Molecular Formula: C₁₀H₁₂ClN₅OS
• Molecular Weight: 285.757
• Mol file: 142941-60-4.mol

Synonyms:

Chemical Property of 2-(2-amino-6-chloro-9H-purin-9-yl)-1,4-anhydro-2,3-dideoxy-1-thio-L-threo-pentitol

Chemical Property:

• Vapor Pressure: 3.45E-16mmHg at 25°C
• Boiling Point: 619.1°Cat760mmHg
• Flash Point: 328.2°C
• Density: 1.89g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(2-amino-6-chloro-9H-purin-9-yl)-1,4-anhydro-2,3-dideoxy-1-thio-L-threo-pentitol

There total 17 articles about 2-(2-amino-6-chloro-9H-purin-9-yl)-1,4-anhydro-2,3-dideoxy-1-thio-L-threo-pentitol 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:

(3'R,5'R)-1-<5'-<(benzyloxy)methyl>tetrahydro-3'-thienyl>-6-chloro-9H-purin-6-amine (142941-56-8) → (2R,4R)-4-(2'-amino-6'-chloro-9'H-purin-9'-yl)tetrahydrothiophene-2-methanol (142941-60-4)

Guidance literature:

With boron tribromide; at -78 ℃;

DOI:10.1016/0040-4039(91)80867-6

Reference yield:

(3R,5S)-5-Benzyloxymethyl-2-methoxy-tetrahydro-furan-3-ol (132813-61-7,132813-62-8,142941-63-7,142941-64-8) → (2R,4R)-4-(2'-amino-6'-chloro-9'H-purin-9'-yl)tetrahydrothiophene-2-methanol (142941-60-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 93 percent / DMAP / CH₂Cl₂ / 1 h / 0 °C

2: 90 percent / CF₃COOH / H₂O; tetrahydrofuran / 5 h

3: 83 percent / NaBH(OAc)3 / toluene / 0.75 h / 80 °C

4: 90 percent / pyridine / CH₂Cl₂ / 18 h / 4 °C

5: 73 percent / Na₂S / dimethylformamide / 3 h / 100 °C

6: 82 percent / diethyl azodicarboxylate, PPh₃ / tetrahydrofuran / 0.83 h / Ambient temperature

7: 81 percent / K₂CO₃ / methanol / 0.5 h

8: 94 percent / DMAP / CH₂Cl₂ / 1 h / 0 °C

9: 26 percent / K₂CO₃ / dimethylsulfoxide / 85 °C

10: 1) BBr₃, 2) aq. NH₃ / 1) CH₂Cl₂, 2) CH₂Cl₂, 45 min

With pyridine; dmap; sodium sulfide; ammonium hydroxide; boron tribromide; sodium tris(acetoxy)borohydride; potassium carbonate; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

Reference yield:

(2R,4S)-2-<(benzyloxy)methyl>-4-<(methylsulfonyl)oxy>tetrahydrothiophene (142941-51-3) → (2R,4R)-4-(2'-amino-6'-chloro-9'H-purin-9'-yl)tetrahydrothiophene-2-methanol (142941-60-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 26 percent / K₂CO₃ / dimethylsulfoxide / 85 °C

2: 1) BBr₃, 2) aq. NH₃ / 1) CH₂Cl₂, 2) CH₂Cl₂, 45 min

With ammonium hydroxide; boron tribromide; potassium carbonate; In dimethyl sulfoxide;

upstream raw materials:

(3'R,5'R)-1-<5'-<(benzyloxy)methyl>tetrahydro-3'-thienyl>-6-chloro-9H-purin-6-amine

(3R,5S)-5-Benzyloxymethyl-2-methoxy-tetrahydro-furan-3-ol

(2R,4S)-2-<(benzyloxy)methyl>-4-<(methylsulfonyl)oxy>tetrahydrothiophene

(2R,4S)-2-benzoyloxy-5-(benzyloxy)pentane-1,4-diol