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

Base Information

• Chemical Name: 9-{(3'S,4'S)-3'-C-[(acetylthio)methyl]-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-β-pentofuranosyl}adenine
• CAS No.: 206982-54-9
• Molecular Formula: C₂₉H₃₅N₅O₃SSi
• Molecular Weight: 561.78
• Mol file: 206982-54-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about 9-{(3'S,4'S)-3'-C-[(acetylthio)methyl]-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-β-pentofuranosyl}adenine 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: 79.0%

tiolacetic acid (507-09-5) + 9-{(3'R,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(hydroxymethyl)-β-pentofuranosyl}adenine (206982-53-8) → 9-{(3'S,4'S)-3'-C-[(acetylthio)methyl]-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-β-pentofuranosyl}adenine (206982-54-9)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran;

DOI:10.1021/ja972768y

Reference yield: 79.0%

thioacetic acid (507-09-5) + 9-{(3'R,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(hydroxymethyl)-β-pentofuranosyl}adenine (206982-53-8) → 9-{(3'S,4'S)-3'-C-[(acetylthio)methyl]-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-β-pentofuranosyl}adenine (206982-54-9)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; for 2h;

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

Reference yield:

(2S,3S,5R)-5-(6-Amino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-carbaldehyde (157729-47-0) → 9-{(3'S,4'S)-3'-C-[(acetylthio)methyl]-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-β-pentofuranosyl}adenine (206982-54-9)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

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

upstream raw materials:

tiolacetic acid

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

thioacetic acid

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

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