6-S-(2-cyanoethyl)-2'-O-(tert-butyldimethylsilyl)-2-N-phenylacetyl-6-thioguanosine

Base Information

Chemical Name:6-S-(2-cyanoethyl)-2'-O-(tert-butyldimethylsilyl)-2-N-phenylacetyl-6-thioguanosine
CAS No.:1054656-15-3
Molecular Formula:C₂₇H₃₆N₆O₅SSi
Molecular Weight:584.772
Hs Code.:

Synonyms:6-S-(2-cyanoethyl)-2'-O-(tert-butyldimethylsilyl)-2-N-phenylacetyl-6-thioguanosine

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Chemical Property of 6-S-(2-cyanoethyl)-2'-O-(tert-butyldimethylsilyl)-2-N-phenylacetyl-6-thioguanosine

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Technology Process of 6-S-(2-cyanoethyl)-2'-O-(tert-butyldimethylsilyl)-2-N-phenylacetyl-6-thioguanosine

There total 6 articles about 6-S-(2-cyanoethyl)-2'-O-(tert-butyldimethylsilyl)-2-N-phenylacetyl-6-thioguanosine 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: 91.0%

: 6-S-(2-cyanoethyl)-2'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-2-N-phenylacetyl-6-thioguanosine

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

Guidance literature:: With dichloro-acetic acid; In dichloromethane; at 20 ℃; for 0.0333333h;
DOI:10.1021/jo991432z

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 6 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

With 1H-imidazole; 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;
DOI:10.1021/jo991432z

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 steps

1: 86 percent / pyridine / 18 h / 20 °C

2: 28 percent / imidazole / dimethylformamide / 16 h / 20 °C

3: 91 percent / Cl₂CHCOOH / CH₂Cl₂ / 0.03 h / 20 °C

With 1H-imidazole; dichloro-acetic acid; In pyridine; dichloromethane; N,N-dimethyl-formamide; 1: Alkylation / 2: silylation / 3: dealkylation;
DOI:10.1021/jo991432z