(7S,6R)-[7-tert-butoxycarbonylamino-6-(tert-butyl-dimethyl-silanyloxy)-8-methyl-non-4-enyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: (7S,6R)-[7-tert-butoxycarbonylamino-6-(tert-butyl-dimethyl-silanyloxy)-8-methyl-non-4-enyl]-carbamic acid benzyl ester
• CAS No.: 677738-22-6
• Molecular Formula: C₂₉H₅₀N₂O₅Si
• Molecular Weight: 534.812
• Mol file: 677738-22-6.mol

Synonyms:(7S,6R)-[7-tert-butoxycarbonylamino-6-(tert-butyl-dimethyl-silanyloxy)-8-methyl-non-4-enyl]-carbamic acid benzyl ester

Chemical Property of (7S,6R)-[7-tert-butoxycarbonylamino-6-(tert-butyl-dimethyl-silanyloxy)-8-methyl-non-4-enyl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (7S,6R)-[7-tert-butoxycarbonylamino-6-(tert-butyl-dimethyl-silanyloxy)-8-methyl-non-4-enyl]-carbamic acid benzyl ester

There total 6 articles about (7S,6R)-[7-tert-butoxycarbonylamino-6-(tert-butyl-dimethyl-silanyloxy)-8-methyl-non-4-enyl]-carbamic acid benzyl 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:

(S)-1-(dimethoxyphosphoryl)-4-methyl-3-(t-butoxycarbonylamino)-pentan-2-one (129301-63-9) → (7S,6R)-[7-tert-butoxycarbonylamino-6-(tert-butyl-dimethyl-silanyloxy)-8-methyl-non-4-enyl]-carbamic acid benzyl ester (677738-22-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 67 percent / K₂CO₃ / ethanol / 6 h

2: 90 percent / NaBH₄ / methanol / 0 °C

3: 80 percent / imidazole / dimethylformamide / 12 h / 20 °C

4: aq. LiOH / tetrahydrofuran / 1 h / 25 °C

5: diphenyl phosphorazidate; Et₃N / toluene / 1 h / Heating

6: 845 mg / toluene / 12 h / Heating

With 1H-imidazole; lithium hydroxide; sodium tetrahydroborate; diphenyl phosphoryl azide; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; toluene; 1: Horner-Emmons olefination / 5: Curtius rearrangement;

DOI:10.1021/ol0499147

Reference yield:

(8S)-8-tert-butoxycarbonylamino-9-methyl-7-oxo-dec-5-enoic acid methyl ester (677738-16-8) → (7S,6R)-[7-tert-butoxycarbonylamino-6-(tert-butyl-dimethyl-silanyloxy)-8-methyl-non-4-enyl]-carbamic acid benzyl ester (677738-22-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / NaBH₄ / methanol / 0 °C

2: 80 percent / imidazole / dimethylformamide / 12 h / 20 °C

3: aq. LiOH / tetrahydrofuran / 1 h / 25 °C

4: diphenyl phosphorazidate; Et₃N / toluene / 1 h / Heating

5: 845 mg / toluene / 12 h / Heating

With 1H-imidazole; lithium hydroxide; sodium tetrahydroborate; diphenyl phosphoryl azide; triethylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene; 4: Curtius rearrangement;

DOI:10.1021/ol0499147

Reference yield:

(8S,7R)-8-tert-butoxycarbonylamino-7-hydroxy-9-methyI-dec-5-enoic acid methyl ester (677738-17-9) → (7S,6R)-[7-tert-butoxycarbonylamino-6-(tert-butyl-dimethyl-silanyloxy)-8-methyl-non-4-enyl]-carbamic acid benzyl ester (677738-22-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / imidazole / dimethylformamide / 12 h / 20 °C

2: aq. LiOH / tetrahydrofuran / 1 h / 25 °C

3: diphenyl phosphorazidate; Et₃N / toluene / 1 h / Heating

4: 845 mg / toluene / 12 h / Heating

With 1H-imidazole; lithium hydroxide; diphenyl phosphoryl azide; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; 3: Curtius rearrangement;

DOI:10.1021/ol0499147

upstream raw materials:

benzyl alcohol

(S)-1-(dimethoxyphosphoryl)-4-methyl-3-(t-butoxycarbonylamino)-pentan-2-one

(8S)-8-tert-butoxycarbonylamino-9-methyl-7-oxo-dec-5-enoic acid methyl ester

(8S,7R)-8-tert-butoxycarbonylamino-7-hydroxy-9-methyI-dec-5-enoic acid methyl ester

Downstream raw materials:

(7S,6R)-(7-tert-butoxycarbonylamino-6-hydroxy-8-methyl-non-4-enyl)-carbamic acid benzyl ester