Thioacetic acid S-[(2S,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ylmethyl] ester

Base Information

• Chemical Name: Thioacetic acid S-[(2S,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ylmethyl] ester
• CAS No.: 206982-55-0
• Molecular Formula: C₃₆H₃₉N₅O₄SSi
• Molecular Weight: 665.888
• Mol file: 206982-55-0.mol

Synonyms:Thioacetic acid S-[(2S,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ylmethyl] ester

Chemical Property of Thioacetic acid S-[(2S,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ylmethyl] ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Thioacetic acid S-[(2S,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ylmethyl] ester

There total 3 articles about Thioacetic acid S-[(2S,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ylmethyl] 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:

(2S,3S,5R)-5-(6-Amino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-carbaldehyde (157729-47-0) → Thioacetic acid S-[(2S,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ylmethyl] ester (206982-55-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / NaBH₄ / ethanol; tetrahydrofuran / 2 h / 20 °C

2: 79 percent / PPh₃; DIAD / tetrahydrofuran / 2 h / 0 - 20 °C

3: N,N-dimethylpyridin-4-amine / pyridine / 1 h / 20 °C

With dmap; sodium tetrahydroborate; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; pyridine; ethanol; 2: Mitsunobu reaction;

DOI:10.1002/1522-2675(200209)85:9<2777::AID-HLCA2777>3.0.CO;2-1

Reference yield:

9-{(3'R,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(hydroxymethyl)-β-pentofuranosyl}adenine (206982-53-8) → Thioacetic acid S-[(2S,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ylmethyl] ester (206982-55-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / PPh₃; DIAD / tetrahydrofuran / 2 h / 0 - 20 °C

2: N,N-dimethylpyridin-4-amine / pyridine / 1 h / 20 °C

With dmap; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; pyridine; 1: Mitsunobu reaction;

DOI:10.1002/1522-2675(200209)85:9<2777::AID-HLCA2777>3.0.CO;2-1

Reference yield:

benzoyl chloride (98-88-4) + 9-{(3'S,4'S)-3'-C-[(acetylthio)methyl]-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-β-pentofuranosyl}adenine (206982-54-9) → Thioacetic acid S-[(2S,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ylmethyl] ester (206982-55-0)

Guidance literature:

With pyridine; dmap;

DOI:10.1021/ja972768y

upstream raw materials:

benzoyl chloride

9-{(3'S,4'S)-3'-C-[(acetylthio)methyl]-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-β-pentofuranosyl}adenine

(2S,3S,5R)-5-(6-Amino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-carbaldehyde

9-{(3'R,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(hydroxymethyl)-β-pentofuranosyl}adenine

Downstream raw materials:

N⁶-benzoyl-5'-O-[(tert-butyl)diphenylsilyl]-2'-deoxy-3'-de(phosphinicooxy)adenylylmethylenesulfonylmethylene-(3'->5')-3'-O-[(tert-butyl)diphenylsilyl]-2',5'-dideoxythymidine

N⁶-benzoyl-2'-deoxy-3'-de(phosphinicooxy)-5'-O-(4,4'-dimethoxytrityl)adenylylmethylenesulfonylmethylene-(3'->5')-2',5'-dideoxythymidine

N⁶-benzoyl-2'-deoxy-3'-de(phosphinicooxy)adenylylmethylenesulfonylmethylene-(3'->5')-2',5'-dideoxythymidine

N⁶-benzoyl-9-{(3'S,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(mercaptomethyl)-β-pentofuranosyl}adenine