6-S-(2-cyanoethyl)-2'-O-(tert-butyldimethylsilyl)-2-N-phenylacetyl-6-thioguanosine 3',5'-bisphosphate tetrakis(2-cyanoethyl) ester

Base Information

Chemical Name:6-S-(2-cyanoethyl)-2'-O-(tert-butyldimethylsilyl)-2-N-phenylacetyl-6-thioguanosine 3',5'-bisphosphate tetrakis(2-cyanoethyl) ester
CAS No.:1053249-50-5
Molecular Formula:C₃₉H₅₀N₁₀O₁₁P₂SSi
Molecular Weight:956.985
Hs Code.:

Synonyms:6-S-(2-cyanoethyl)-2'-O-(tert-butyldimethylsilyl)-2-N-phenylacetyl-6-thioguanosine 3',5'-bisphosphate tetrakis(2-cyanoethyl) ester

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Chemical Property of 6-S-(2-cyanoethyl)-2'-O-(tert-butyldimethylsilyl)-2-N-phenylacetyl-6-thioguanosine 3',5'-bisphosphate tetrakis(2-cyanoethyl) ester

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Technology Process of 6-S-(2-cyanoethyl)-2'-O-(tert-butyldimethylsilyl)-2-N-phenylacetyl-6-thioguanosine 3',5'-bisphosphate tetrakis(2-cyanoethyl) ester

There total 7 articles about 6-S-(2-cyanoethyl)-2'-O-(tert-butyldimethylsilyl)-2-N-phenylacetyl-6-thioguanosine 3',5'-bisphosphate tetrakis(2-cyanoethyl) 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: 78.0%

: 102690-88-0
bis(2-cyanoethyl) diisopropylamidophosphite

: 1054656-15-3
6-S-(2-cyanoethyl)-2'-O-(tert-butyldimethylsilyl)-2-N-phenylacetyl-6-thioguanosine

: 1053249-50-5
6-S-(2-cyanoethyl)-2'-O-(tert-butyldimethylsilyl)-2-N-phenylacetyl-6-thioguanosine 3',5'-bisphosphate tetrakis(2-cyanoethyl) ester

Guidance literature:: bis(2-cyanoethyl) diisopropylamidophosphite; 6-S-(2-cyanoethyl)-2'-O-(tert-butyldimethylsilyl)-2-N-phenylacetyl-6-thioguanosine; With 1H-tetrazole; In acetonitrile; at 20 ℃; for 1h;

With tert.-butylhydroperoxide; In acetonitrile; at 20 ℃; for 0.5h; Further stages.;
DOI:10.1021/jo991432z

Reference yield:

: 132628-16-1
2-N-(phenylacetyl)-9-(β-D-ribofuranosyl)-guanine

: 1053249-50-5
6-S-(2-cyanoethyl)-2'-O-(tert-butyldimethylsilyl)-2-N-phenylacetyl-6-thioguanosine 3',5'-bisphosphate tetrakis(2-cyanoethyl) ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: acetonitrile / 2 h / Heating

2.1: Et₃N; 4-(dimethylamino)pyridine; 2,4,6-trimethylbenzenesulfonyl chloride / CH₂Cl₂ / 1 h / 20 °C

2.2: N-methylpyrrolidine / CH₂Cl₂ / 0.5 h / 0 °C

3.1: 943 mg / CF₃COOH / methanol / 0.33 h / 20 °C

4.1: 86 percent / pyridine / 18 h / 20 °C

5.1: 28 percent / imidazole / dimethylformamide / 16 h / 20 °C

6.1: 91 percent / Cl₂CHCOOH / CH₂Cl₂ / 0.03 h / 20 °C

7.1: 1H-tetrazole / acetonitrile / 1 h / 20 °C

7.2: 78 percent / t-BuOOH / acetonitrile / 0.5 h / 20 °C

With 1H-imidazole; 1H-tetrazole; dichloro-acetic acid; dmap; 2-mesitylenesulphonyl chloride; triethylamine; trifluoroacetic acid; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: silylation / 2.1: sulfonation / 2.2: Substitution / 3.1: desilylation / 4.1: Alkylation / 5.1: silylation / 6.1: dealkylation / 7.1: Substitution / 7.2: Oxidation;
DOI:10.1021/jo991432z

Reference yield:

: 1053737-66-8
6-S-(2-cyanoethyl)-2-N-phenylacetyl-6-thioguanosine

: 1053249-50-5
6-S-(2-cyanoethyl)-2'-O-(tert-butyldimethylsilyl)-2-N-phenylacetyl-6-thioguanosine 3',5'-bisphosphate tetrakis(2-cyanoethyl) ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 86 percent / pyridine / 18 h / 20 °C

2.1: 28 percent / imidazole / dimethylformamide / 16 h / 20 °C

3.1: 91 percent / Cl₂CHCOOH / CH₂Cl₂ / 0.03 h / 20 °C

4.1: 1H-tetrazole / acetonitrile / 1 h / 20 °C

4.2: 78 percent / t-BuOOH / acetonitrile / 0.5 h / 20 °C

With 1H-imidazole; 1H-tetrazole; dichloro-acetic acid; In pyridine; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Alkylation / 2.1: silylation / 3.1: dealkylation / 4.1: Substitution / 4.2: Oxidation;
DOI:10.1021/jo991432z