(+)-2-amino-9-[(1S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-L-ribofuranosyl]-6-chloropurine

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Chemical Name:(+)-2-amino-9-[(1S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-L-ribofuranosyl]-6-chloropurine
CAS No.:479036-19-6
Molecular Formula:C₂₆H₂₇ClFN₅OSSi
Molecular Weight:540.136
Hs Code.:

Synonyms:(+)-2-amino-9-[(1S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-L-ribofuranosyl]-6-chloropurine

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Chemical Property of (+)-2-amino-9-[(1S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-L-ribofuranosyl]-6-chloropurine

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Technology Process of (+)-2-amino-9-[(1S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-L-ribofuranosyl]-6-chloropurine

There total 14 articles about (+)-2-amino-9-[(1S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-L-ribofuranosyl]-6-chloropurine 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:

: 212954-52-4
(R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-fluoro-5H-furan-2-one

: 479036-19-6
(+)-2-amino-9-[(1S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-L-ribofuranosyl]-6-chloropurine

Guidance literature:: Multi-step reaction with 12 steps

1.1: 95 percent / H₂ / 5percent Pd/C / ethyl acetate / 3 h

2.1: aq. NaOH / ethanol / 2 h / 20 °C

3.1: dimethylsulfoxide / 1 h

4.1: 82 percent / I₂; Ph₃P; imidazole / toluene / 4 h / 60 °C

5.1: 91 percent / dimethylformamide / 8 h / 20 °C

6.1: DIBAL-H / hexane; toluene / 1 h / -78 °C

7.1: Ac₂O; DMSO / 24 h / 20 °C

8.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C

8.2: TMSCl / tetrahydrofuran / 20 °C

8.3: 74 percent / tetrahydrofuran / 1 h / -78 °C

9.1: DIBAL-H / toluene; hexane / 1 h / -78 °C

10.1: TEA; 4-DMAP / CH₂Cl₂ / 3 h / 20 °C

11.1: TMSOTf / 1,2-dichloro-ethane / 16 h / -25 - 40 °C

12.1: mCPBA / CH₂Cl₂ / 0.5 h / -78 °C

12.2: pyridine / CH₂Cl₂ / 2 h / 20 °C

12.3: NH₃ gas / 1,2-dimethoxy-ethane / 5 h / 20 °C

With 1H-imidazole; dmap; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; TEA; hydrogen; iodine; acetic anhydride; diisobutylaluminium hydride; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; 5percent Pd/C; In tetrahydrofuran; ethanol; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 4.1: Mitsunobu reaction / 7.1: Moffatt-type oxidation;
DOI:10.1021/jm020376i

Reference yield:

: 479036-14-1
(-)-9-[(1S,2S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranosyl]-6-chloro-2-fluoropurine

: 479036-19-6
(+)-2-amino-9-[(1S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-L-ribofuranosyl]-6-chloropurine

: 6-amino-9-[(1S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-L-ribofuranosyl]-2-fluoropurine

: 6-amino-9-[(4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-1,2-didehydro-2-fluoro-4-thio-β-L-ribofuranosyl]-2-fluoropurine

Guidance literature:: (-)-9-[(1S,2S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranosyl]-6-chloro-2-fluoropurine; With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃; for 0.5h;

With pyridine; In dichloromethane; at 20 ℃; for 2h;

With ammonia; In 1,2-dimethoxyethane; at 20 ℃; for 5h; Further stages.;
DOI:10.1021/jm020376i

Reference yield:

: 1651-29-2
6-chloro-2-fluoropurine

: 479036-19-6
(+)-2-amino-9-[(1S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-L-ribofuranosyl]-6-chloropurine

Guidance literature:: Multi-step reaction with 3 steps

1.1: ammonium sulfate / 5 h / Heating

2.1: TMSOTf / 1,2-dichloro-ethane / 16 h / -25 - 40 °C

3.1: mCPBA / CH₂Cl₂ / 0.5 h / -78 °C

3.2: pyridine / CH₂Cl₂ / 2 h / 20 °C

3.3: NH₃ gas / 1,2-dimethoxy-ethane / 5 h / 20 °C

With ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; 1,2-dichloro-ethane;
DOI:10.1021/jm020376i