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

Base Information

• Chemical Name: N⁶-benzoyl-2'-deoxy-3'-de(phosphinicooxy)-5'-O-(4,4'-dimethoxytrityl)adenylylmethylenesulfonylmethylene-(3'->5')-2',5'-dideoxythymidine
• CAS No.: 206982-59-4
• Molecular Formula: C₅₀H₅₁N₇O₁₁S
• Molecular Weight: 958.061

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

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

Chemical Property:

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

There total 15 articles about N⁶-benzoyl-2'-deoxy-3'-de(phosphinicooxy)-5'-O-(4,4'-dimethoxytrityl)adenylylmethylenesulfonylmethylene-(3'->5')-2',5'-dideoxythymidine 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: 66.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + N6-benzoyl-2'-deoxy-3'-de(phosphinicooxy)adenylylmethylenesulfonylmethylene-(3'->5')-2',5'-dideoxythymidine (206982-58-3) → N6-benzoyl-2'-deoxy-3'-de(phosphinicooxy)-5'-O-(4,4'-dimethoxytrityl)adenylylmethylenesulfonylmethylene-(3'->5')-2',5'-dideoxythymidine (206982-59-4)

Guidance literature:

With pyridine; dmap; TEA;

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-2'-deoxy-3'-de(phosphinicooxy)-5'-O-(4,4'-dimethoxytrityl)adenylylmethylenesulfonylmethylene-(3'->5')-2',5'-dideoxythymidine (206982-59-4)

Guidance literature:

Multi-step reaction with 8 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

5: Cs₂CO₃ / tetrahydrofuran; dimethylformamide / 20 °C

6: 983 mg / Oxone; AcONa / tetrahydrofuran; methanol; H₂O / 2 h / 20 °C

7: 75 percent / HF / pyridine / 20 h / 20 °C

8: 66 percent / Et₃N; DMAP / pyridine / 2 h / 20 °C

With dmap; Oxone; sodium hydroxide; sodium tetrahydroborate; di-isopropyl azodicarboxylate; hydrogen fluoride; sodium acetate; caesium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; ethanol; water; N,N-dimethyl-formamide; 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) → N6-benzoyl-2'-deoxy-3'-de(phosphinicooxy)-5'-O-(4,4'-dimethoxytrityl)adenylylmethylenesulfonylmethylene-(3'->5')-2',5'-dideoxythymidine (206982-59-4)

Guidance literature:

Multi-step reaction with 7 steps

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

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

3: 937 mg / aq. NaOH / pyridine; ethanol / 0.17 h / 20 °C

4: Cs₂CO₃ / tetrahydrofuran; dimethylformamide / 20 °C

5: 983 mg / Oxone; AcONa / tetrahydrofuran; methanol; H₂O / 2 h / 20 °C

6: 75 percent / HF / pyridine / 20 h / 20 °C

7: 66 percent / Et₃N; DMAP / pyridine / 2 h / 20 °C

With dmap; Oxone; sodium hydroxide; di-isopropyl azodicarboxylate; hydrogen fluoride; sodium acetate; caesium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; ethanol; water; N,N-dimethyl-formamide; 1: Mitsunobu reaction;

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

upstream raw materials:

4,4'-dimethoxytrityl chloride

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

benzoyl chloride

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

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