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

Base Information

• Chemical Name: N⁶-benzoyl-9-{(3'S,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(mercaptomethyl)-β-pentofuranosyl}adenine
• CAS No.: 206982-56-1
• Molecular Formula: C₃₄H₃₇N₅O₃SSi
• Molecular Weight: 623.851

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

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

Chemical Property:

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

There total 6 articles about N⁶-benzoyl-9-{(3'S,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(mercaptomethyl)-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:

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) → N6-benzoyl-9-{(3'S,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(mercaptomethyl)-β-pentofuranosyl}adenine (206982-56-1)

Guidance literature:

With pyridine; sodium hydroxide; In ethanol; Yield given;

DOI:10.1021/ja972768y

Reference yield:

(2S,3S,5R)-5-(6-Amino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-carbaldehyde (157729-47-0) → N6-benzoyl-9-{(3'S,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(mercaptomethyl)-β-pentofuranosyl}adenine (206982-56-1)

Guidance literature:

Multi-step reaction with 4 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

4: 937 mg / aq. NaOH / pyridine; ethanol / 0.17 h / 20 °C

With dmap; sodium hydroxide; 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'S,4'S)-3'-C-[(acetylthio)methyl]-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-β-pentofuranosyl}adenine (206982-54-9) → N6-benzoyl-9-{(3'S,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(mercaptomethyl)-β-pentofuranosyl}adenine (206982-56-1)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 937 mg / aq. NaOH / pyridine; ethanol / 0.17 h / 20 °C

With dmap; sodium hydroxide; In pyridine; ethanol;

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

upstream raw materials:

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

benzoyl chloride

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

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

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

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