Imidazole-1-carbothioic acid O-[(2R,3S,5R)-5-(6-amino-8-benzyloxy-purin-9-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl] ester

Base Information

• Chemical Name: Imidazole-1-carbothioic acid O-[(2R,3S,5R)-5-(6-amino-8-benzyloxy-purin-9-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl] ester
• CAS No.: 131283-75-5
• Molecular Formula: C₂₇H₃₅N₇O₄SSi
• Molecular Weight: 581.771
• Mol file: 131283-75-5.mol

Synonyms:

Chemical Property of Imidazole-1-carbothioic acid O-[(2R,3S,5R)-5-(6-amino-8-benzyloxy-purin-9-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl] ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Imidazole-1-carbothioic acid O-[(2R,3S,5R)-5-(6-amino-8-benzyloxy-purin-9-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl] ester

There total 7 articles about Imidazole-1-carbothioic acid O-[(2R,3S,5R)-5-(6-amino-8-benzyloxy-purin-9-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl] 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:

8-Benzyloxyadenosine (131265-29-7) → Imidazole-1-carbothioic acid O-[(2R,3S,5R)-5-(6-amino-8-benzyloxy-purin-9-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl] ester (131283-75-5)

Guidance literature:

Multi-step reaction with 4 steps

1: N,N-dimethylaminopyridine, NEt₃ / dimethylformamide; CH₂Cl₂ / 12 h / Ambient temperature

2: dimethylformamide / 6 h / Ambient temperature

3: tributyltin hydride, 2,2'-azobis(2-methylpropionitrile) / toluene / 2.5 h / Heating

4: dimethylformamide / 5 h / 90 °C

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1055/s-1990-27066

Reference yield:

(2R,3R,4S,5R)-2-(6-Amino-8-benzyloxy-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3,4-diol (131265-32-2) → Imidazole-1-carbothioic acid O-[(2R,3S,5R)-5-(6-amino-8-benzyloxy-purin-9-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl] ester (131283-75-5)

Guidance literature:

Multi-step reaction with 3 steps

1: dimethylformamide / 6 h / Ambient temperature

2: tributyltin hydride, 2,2'-azobis(2-methylpropionitrile) / toluene / 2.5 h / Heating

3: dimethylformamide / 5 h / 90 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In N,N-dimethyl-formamide; toluene;

DOI:10.1055/s-1990-27066

Reference yield:

(3aR,4R,6R,6aR)-4-(6-Amino-8-benzyloxy-purin-9-yl)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furo[3,4-d][1,3]dioxole-2-thione (131707-95-4) → Imidazole-1-carbothioic acid O-[(2R,3S,5R)-5-(6-amino-8-benzyloxy-purin-9-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl] ester (131283-75-5)

Guidance literature:

Multi-step reaction with 2 steps

1: tributyltin hydride, 2,2'-azobis(2-methylpropionitrile) / toluene / 2.5 h / Heating

2: dimethylformamide / 5 h / 90 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In N,N-dimethyl-formamide; toluene;

DOI:10.1055/s-1990-27066

upstream raw materials:

(2R,3S,5R)-5-(6-Amino-8-benzyloxy-purin-9-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-ol

1,1'-Thiocarbonyldiimidazole

8-Benzyloxyadenosine

(2R,3R,4S,5R)-2-(6-Amino-8-benzyloxy-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3,4-diol

Downstream raw materials:

8-Benzyloxy-5'-O-tert-butyldimethylsilyl-2',3'-dideoxyadenosine

8-Benzyloxy-2',3'-dideoxyadenosine