(E)-(S)-1-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hept-5-en-3-ol

Base Information

• Chemical Name: (E)-(S)-1-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hept-5-en-3-ol
• CAS No.: 274693-87-7
• Molecular Formula: C₂₁H₃₆O₃Si
• Molecular Weight: 364.601
• Mol file: 274693-87-7.mol

Synonyms:(E)-(S)-1-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hept-5-en-3-ol

Chemical Property of (E)-(S)-1-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hept-5-en-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(S)-1-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hept-5-en-3-ol

There total 1 articles about (E)-(S)-1-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hept-5-en-3-ol 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: 91.0%

(2R)-2-(2-benzyloxyethyl)oxirane (115114-87-9) + (E)-2-bromo-4-(tert-butyldimethylsilyloxy)-2-butene (143236-64-0) → (E)-(S)-1-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hept-5-en-3-ol (274693-87-7)

Guidance literature:

(E)-2-bromo-4-(tert-butyldimethylsilyloxy)-2-butene; With tert.-butyl lithium; In diethyl ether; at -78 ℃; for 1h;

In diethyl ether; for 0.333333h;

(2R)-2-(2-benzyloxyethyl)oxirane; In tetrahydrofuran; at -78 - 20 ℃; for 12h;

DOI:10.1016/S0040-4039(00)00208-2

Reference yield:

(E)-(S)-1-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hept-5-en-3-ol (274693-87-7) → (E)-(2S,4R,9S,11R,12S)-11,13-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-4,11,12-trimethyl-9-triisopropylsilanyloxy-tridec-5-en-7-one (274693-96-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: TEA / CH₂Cl₂ / 0.17 h / 0 °C

2.1: 87 percent / HF-Pyr; pyridine / tetrahydrofuran / 2 h / 0 - 20 °C

3.1: Ti(O-i-Pr)4; D-(-)-DET; TBHP / CH₂Cl₂ / 7 h / -20 °C

4.1: 73 percent / DMAP; TEA / CH₂Cl₂ / 4 h / 0 - 20 °C

5.1: 100 percent / diethyl ether / 12 h / -78 - 20 °C

6.1: 85 percent / TEA / CH₂Cl₂ / 2 h / 0 - 20 °C

7.1: 90 percent / hydrogen / Pd/C / ethanol / 0.33 h / 20 °C

8.1: (COCl)2; DMSO; TEA / CH₂Cl₂ / 0.58 h / -78 - 20 °C

9.1: t-BuLi / 0.25 h / -78 °C

9.2: 733 percent / tetrahydrofuran / 0.33 h / -78 °C

10.1: 86 percent / Dess-Martin periodinane / pyridine; CH₂Cl₂ / 48 h / 20 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; oxalyl dichloride; diethyl (2S,3S)-tartrate; TEA; hydrogen fluoride; hydrogen; tert.-butyl lithium; Dess-Martin periodane; dimethyl sulfoxide; palladium on activated charcoal; In tetrahydrofuran; pyridine; diethyl ether; ethanol; dichloromethane; 1.1: Etherification / 2.1: Hydrolysis / 3.1: Epoxidation / 4.1: Etherification / 5.1: Methylation / 6.1: Etherification / 7.1: Hydrogenolysis / 8.1: Oxidation / 9.1: Metallation / 9.2: Alkylation / 10.1: Oxidation;

DOI:10.1016/S0040-4039(00)00208-2

Reference yield:

(E)-(S)-1-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hept-5-en-3-ol (274693-87-7) → (E)-(2S,4R,9R,11R,12S)-11,13-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-4,11,12-trimethyl-9-triisopropylsilanyloxy-tridec-5-en-7-ol (274693-95-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: TEA / CH₂Cl₂ / 0.17 h / 0 °C

2.1: 87 percent / HF-Pyr; pyridine / tetrahydrofuran / 2 h / 0 - 20 °C

3.1: Ti(O-i-Pr)4; D-(-)-DET; TBHP / CH₂Cl₂ / 7 h / -20 °C

4.1: 73 percent / DMAP; TEA / CH₂Cl₂ / 4 h / 0 - 20 °C

5.1: 100 percent / diethyl ether / 12 h / -78 - 20 °C

6.1: 85 percent / TEA / CH₂Cl₂ / 2 h / 0 - 20 °C

7.1: 90 percent / hydrogen / Pd/C / ethanol / 0.33 h / 20 °C

8.1: (COCl)2; DMSO; TEA / CH₂Cl₂ / 0.58 h / -78 - 20 °C

9.1: t-BuLi / 0.25 h / -78 °C

9.2: 733 percent / tetrahydrofuran / 0.33 h / -78 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; oxalyl dichloride; diethyl (2S,3S)-tartrate; TEA; hydrogen fluoride; hydrogen; tert.-butyl lithium; dimethyl sulfoxide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; 1.1: Etherification / 2.1: Hydrolysis / 3.1: Epoxidation / 4.1: Etherification / 5.1: Methylation / 6.1: Etherification / 7.1: Hydrogenolysis / 8.1: Oxidation / 9.1: Metallation / 9.2: Alkylation;

DOI:10.1016/S0040-4039(00)00208-2

upstream raw materials:

(2R)-2-(2-benzyloxyethyl)oxirane

(E)-2-bromo-4-(tert-butyldimethylsilyloxy)-2-butene

Downstream raw materials:

[(E)-(S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-3-triisopropylsilanyloxy-hept-5-enyloxymethyl]-benzene

(E)-(S)-7-Benzyloxy-3-methyl-5-triisopropylsilanyloxy-hept-2-en-1-ol

[(2R,3R)-3-((R)-4-Benzyloxy-2-triisopropylsilanyloxy-butyl)-3-methyl-oxiranyl]-methanol

(2R,3R)-2-((R)-4-Benzyloxy-2-triisopropylsilanyloxy-butyl)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-oxirane

Refernces