4(S)-(2-amino-6-chloro-9H-purin-9-yl)-2(S)-(O-benzoylmethyl)tetrahydrofuran

Base Information

• Chemical Name: 4(S)-(2-amino-6-chloro-9H-purin-9-yl)-2(S)-(O-benzoylmethyl)tetrahydrofuran
• CAS No.: 160999-07-5
• Molecular Formula: C₁₇H₁₆ClN₅O₃
• Molecular Weight: 373.799
• Mol file: 160999-07-5.mol

Synonyms:4(S)-(2-amino-6-chloro-9H-purin-9-yl)-2(S)-(O-benzoylmethyl)tetrahydrofuran

Chemical Property of 4(S)-(2-amino-6-chloro-9H-purin-9-yl)-2(S)-(O-benzoylmethyl)tetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4(S)-(2-amino-6-chloro-9H-purin-9-yl)-2(S)-(O-benzoylmethyl)tetrahydrofuran

There total 8 articles about 4(S)-(2-amino-6-chloro-9H-purin-9-yl)-2(S)-(O-benzoylmethyl)tetrahydrofuran 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: 58.1%

1,4-anhydro-5-O-benzoyl-3-deoxy-2-O-p-toluenesulfonyl-D-ribitol (143191-76-8) + 2-Amino-6-chloropurin (10310-21-1) → 4(S)-(2-amino-6-chloro-9H-purin-9-yl)-2(S)-(O-benzoylmethyl)tetrahydrofuran (160999-07-5)

Guidance literature:

With 18-crown-6 ether; potassium carbonate; In N,N-dimethyl-formamide; at 70 ℃;

DOI:10.1080/07328319608002371

Reference yield:

[(3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate (4105-29-7) → 4(S)-(2-amino-6-chloro-9H-purin-9-yl)-2(S)-(O-benzoylmethyl)tetrahydrofuran (160999-07-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 77 percent / hydrogen chloride / methanol / 12 h / Ambient temperature

2: 1.) chlorotrimethylsilane; 2.) triethylsilane, TMS-triflate / 1.) 1,1,1,3,3,3-hexamethyldisilazane, reflux, 17 h; 2.) CH₃CN, r.t., 17 h

3: 89 percent / pyridine / 31 h / 5 °C

4: 54 percent / potassium carbonate, 18-crown-6 / dimethylformamide / 11 h / 75 °C / 0 dec C, 2 h; r.t., 46 h

With hydrogenchloride; triethylsilane; chloro-trimethyl-silane; 18-crown-6 ether; trimethylsilyl trifluoromethanesulfonate; potassium carbonate; In pyridine; methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)85259-5

Reference yield:

benzoyl chloride (98-88-4) → 4(S)-(2-amino-6-chloro-9H-purin-9-yl)-2(S)-(O-benzoylmethyl)tetrahydrofuran (160999-07-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 76 percent / pyridine / 0.5 h / -20 - 0 °C

2: 91 percent / CH₂Cl₂ / 4 h / Heating

3: 91 percent / Bu₃Sn, 2,2'-azobis(2-methylpropionitrile) / toluene / 2 h / Heating

4: 77 percent / hydrogen chloride / methanol / 12 h / Ambient temperature

5: 1.) chlorotrimethylsilane; 2.) triethylsilane, TMS-triflate / 1.) 1,1,1,3,3,3-hexamethyldisilazane, reflux, 17 h; 2.) CH₃CN, r.t., 17 h

6: 89 percent / pyridine / 31 h / 5 °C

7: 54 percent / potassium carbonate, 18-crown-6 / dimethylformamide / 11 h / 75 °C / 0 dec C, 2 h; r.t., 46 h

With hydrogenchloride; triethylsilane; chloro-trimethyl-silane; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; potassium carbonate; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)85259-5

upstream raw materials:

1,4-anhydro-5-O-benzoyl-3-deoxy-2-O-p-toluenesulfonyl-D-ribitol

2-Amino-6-chloropurin

[(3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate

benzoyl chloride

Downstream raw materials:

Benzoic acid (2S,4S)-4-(2-amino-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester