9-[3-azido-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-2-yl]-6-chloro-9H-purine

Base Information

Chemical Name:9-[3-azido-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-2-yl]-6-chloro-9H-purine
CAS No.:335260-04-3
Molecular Formula:C₂₆H₂₈ClN₇OSSi
Molecular Weight:550.159
Hs Code.:

9-[3-azido-5-(<i>tert</i>-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-2-yl]-6-chloro-9<i>H</i>-purine

Synonyms:9-[3-azido-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-2-yl]-6-chloro-9H-purine

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Chemical Property of 9-[3-azido-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-2-yl]-6-chloro-9H-purine

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Technology Process of 9-[3-azido-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-2-yl]-6-chloro-9H-purine

There total 12 articles about 9-[3-azido-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-2-yl]-6-chloro-9H-purine 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: 71.0%

: 335259-78-4
Acetic acid (3S,5R)-3-azido-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-2-yl ester

: 335260-04-3
9-[3-azido-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-2-yl]-6-chloro-9H-purine

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 20 - 60 ℃; for 24h;
DOI:10.1016/S0960-894X(01)00006-3

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 335260-04-3
9-[3-azido-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-2-yl]-6-chloro-9H-purine

Guidance literature:: Multi-step reaction with 8 steps

1.1: 76 percent / imidazole / dimethylformamide / 1.5 h / 20 °C

2.1: DMAP / acetonitrile / 24 h / 20 °C

3.1: Et₃B; n-Bu₃SnH / benzene / 0 °C

4.1: 78 percent / NH₃ / methanol / 24 h / 20 °C

5.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 24 h / 40 °C

6.1: 84 percent / NaN₃ / dimethylformamide / 72 h / 40 °C

7.1: mCPBA / CH₂Cl₂ / 3 h / -78 °C

7.2: 24 h / 100 °C

8.1: 71 percent / TMSOTf / 1,2-dichloro-ethane / 24 h / 20 - 60 °C

With 1H-imidazole; dmap; sodium azide; triethyl borane; trimethylsilyl trifluoromethanesulfonate; ammonia; tri-n-butyl-tin hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1016/S0960-894X(01)00006-3

Reference yield:

: 218601-17-3
Benzoic acid (3R,4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-thiophen-3-yl ester

: 335260-04-3
9-[3-azido-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-2-yl]-6-chloro-9H-purine

Guidance literature:: Multi-step reaction with 7 steps

1.1: DMAP / acetonitrile / 24 h / 20 °C

2.1: Et₃B; n-Bu₃SnH / benzene / 0 °C

3.1: 78 percent / NH₃ / methanol / 24 h / 20 °C

4.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 24 h / 40 °C

5.1: 84 percent / NaN₃ / dimethylformamide / 72 h / 40 °C

6.1: mCPBA / CH₂Cl₂ / 3 h / -78 °C

6.2: 24 h / 100 °C

7.1: 71 percent / TMSOTf / 1,2-dichloro-ethane / 24 h / 20 - 60 °C

With dmap; sodium azide; triethyl borane; trimethylsilyl trifluoromethanesulfonate; ammonia; tri-n-butyl-tin hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1016/S0960-894X(01)00006-3