(3R,4S,7S)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-methyl-oxepan-2-one

Base Information

• Chemical Name: (3R,4S,7S)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-methyl-oxepan-2-one
• CAS No.: 906560-64-3
• Molecular Formula: C₃₂H₅₀O₄Si₂
• Molecular Weight: 554.918
• Mol file: 906560-64-3.mol

Synonyms:(3R,4S,7S)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-methyl-oxepan-2-one

Chemical Property of (3R,4S,7S)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-methyl-oxepan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,7S)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-methyl-oxepan-2-one

There total 9 articles about (3R,4S,7S)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-methyl-oxepan-2-one 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: 87.0%

(2R,3S,6S,8S)-3-(tert-butyldimethylsilyloxy)-8-(tert-butyldiphenylsilyloxy)-6-hydroxy-2-methylnonanoic acid (906560-63-2) → (3R,4S,7S)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-methyl-oxepan-2-one (906560-64-3)

Guidance literature:

With dmap; 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/jo060314q

Reference yield:

(4S,6S)-6-(tert-butyldiphenylsilyloxy)-hept-1-en-4-ol (906560-57-4) → (3R,4S,7S)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-methyl-oxepan-2-one (906560-64-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 83 percent / CF₃SO₃H / CH₂Cl₂ / 3 h / 20 °C

2.1: 9-BBN / tetrahydrofuran / 18 h / 20 °C

2.2: 77 percent / aq. NaOH; aq. H₂O / tetrahydrofuran; methanol / 1 h / 50 °C

3.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 0 °C

4.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 1 h / 0 °C

4.2: 1.19 g / CH₂Cl₂ / 18 h / 0 °C

5.1: 85 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

6.1: 76 percent / LiOH*H₂O; aq. H₂O₂ / tetrahydrofuran; H₂O / 24 h / 20 °C

7.1: 84 percent / H₂ / Pd/C / ethyl acetate / 2 h / 20 °C

8.1: 87 percent / i-Pr₂NEt; DMAP; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 20 °C

With 2,6-dimethylpyridine; dmap; lithium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; 2,4,6-trichlorobenzoyl chloride; hydrogen; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; 3.1: Swern oxidation;

DOI:10.1021/jo060314q

Reference yield:

(4S,6S)-4-benzyloxy-6-(tert-butyldiphenylsilyloxy)-hept-1-ene (906560-58-5) → (3R,4S,7S)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-methyl-oxepan-2-one (906560-64-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 9-BBN / tetrahydrofuran / 18 h / 20 °C

1.2: 77 percent / aq. NaOH; aq. H₂O / tetrahydrofuran; methanol / 1 h / 50 °C

2.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 0 °C

3.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 1 h / 0 °C

3.2: 1.19 g / CH₂Cl₂ / 18 h / 0 °C

4.1: 85 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

5.1: 76 percent / LiOH*H₂O; aq. H₂O₂ / tetrahydrofuran; H₂O / 24 h / 20 °C

6.1: 84 percent / H₂ / Pd/C / ethyl acetate / 2 h / 20 °C

7.1: 87 percent / i-Pr₂NEt; DMAP; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 20 °C

With 2,6-dimethylpyridine; dmap; lithium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; 2,4,6-trichlorobenzoyl chloride; hydrogen; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; 2.1: Swern oxidation;

DOI:10.1021/jo060314q

upstream raw materials:

(2R,3S,6S,8S)-3-(tert-butyldimethylsilyloxy)-8-(tert-butyldiphenylsilyloxy)-6-hydroxy-2-methylnonanoic acid

(4S,6S)-6-(tert-butyldiphenylsilyloxy)-hept-1-en-4-ol

(4S,6S)-4-benzyloxy-6-(tert-butyldiphenylsilyloxy)-hept-1-ene

(4S,6S)-4-benzyloxy-6-(tert-butyldiphenylsilyloxy)-heptan-1-ol