Thiocarbonic acid O-{(2R,3R,5S)-2-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-5-methylcarbamoyl-tetrahydro-furan-3-yl} ester O-phenyl ester

Base Information

• Chemical Name: Thiocarbonic acid O-{(2R,3R,5S)-2-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-5-methylcarbamoyl-tetrahydro-furan-3-yl} ester O-phenyl ester
• CAS No.: 874882-65-2
• Molecular Formula: C₂₅H₂₂ClIN₆O₄S
• Molecular Weight: 664.911

Synonyms:

Chemical Property of Thiocarbonic acid O-{(2R,3R,5S)-2-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-5-methylcarbamoyl-tetrahydro-furan-3-yl} ester O-phenyl ester

Chemical Property:

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Technology Process of Thiocarbonic acid O-{(2R,3R,5S)-2-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-5-methylcarbamoyl-tetrahydro-furan-3-yl} ester O-phenyl ester

There total 6 articles about Thiocarbonic acid O-{(2R,3R,5S)-2-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-5-methylcarbamoyl-tetrahydro-furan-3-yl} ester O-phenyl ester 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-iodobenzylamine hydrochloride (3718-88-5) → Thiocarbonic acid O-{(2R,3R,5S)-2-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-5-methylcarbamoyl-tetrahydro-furan-3-yl} ester O-phenyl ester (874882-65-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 57 percent / triethylamine / ethanol / 120 h / Ambient temperature

2: ammonium sulfate / 2 h / Heating

3: TMS triflate / 1,2-dichloro-ethane / 17 h / 90 °C

4: 43 percent / NH₃ / methanol / 18 h / Ambient temperature

5: DMAP / acetonitrile / 6.5 h / Ambient temperature

With dmap; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; ammonia; triethylamine; In methanol; ethanol; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1021/jm00010a017

Reference yield:

2,6 dichloropurine (5451-40-1) → Thiocarbonic acid O-{(2R,3R,5S)-2-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-5-methylcarbamoyl-tetrahydro-furan-3-yl} ester O-phenyl ester (874882-65-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 57 percent / triethylamine / ethanol / 120 h / Ambient temperature

2: ammonium sulfate / 2 h / Heating

3: TMS triflate / 1,2-dichloro-ethane / 17 h / 90 °C

4: 43 percent / NH₃ / methanol / 18 h / Ambient temperature

5: DMAP / acetonitrile / 6.5 h / Ambient temperature

With dmap; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; ammonia; triethylamine; In methanol; ethanol; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1021/jm00010a017

Reference yield:

2-chloro-N-6-(3-iodobenzyl)adenine (120046-86-8) → Thiocarbonic acid O-{(2R,3R,5S)-2-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-5-methylcarbamoyl-tetrahydro-furan-3-yl} ester O-phenyl ester (874882-65-2)

Guidance literature:

Multi-step reaction with 4 steps

1: ammonium sulfate / 2 h / Heating

2: TMS triflate / 1,2-dichloro-ethane / 17 h / 90 °C

3: 43 percent / NH₃ / methanol / 18 h / Ambient temperature

4: DMAP / acetonitrile / 6.5 h / Ambient temperature

With dmap; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; ammonia; In methanol; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1021/jm00010a017

upstream raw materials:

2-chloro-9-<3-deoxy-5-(methylcarbamoyl)-β-D-ribofuranosyl>-N⁶-(3-iodobenzyl)adenine

phenylcarbonochloridothioate

3-iodobenzylamine hydrochloride

2,6 dichloropurine

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