5-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-2,4-dimethyl-hept-2-en-1-ol

Base Information

• Chemical Name: 5-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-2,4-dimethyl-hept-2-en-1-ol
• CAS No.: 918868-28-7
• Molecular Formula: C₃₂H₅₂O₄Si₂
• Molecular Weight: 556.933
• Mol file: 918868-28-7.mol

Synonyms:5-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-2,4-dimethyl-hept-2-en-1-ol

Chemical Property of 5-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-2,4-dimethyl-hept-2-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-2,4-dimethyl-hept-2-en-1-ol

There total 13 articles about 5-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-2,4-dimethyl-hept-2-en-1-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: 94.0%

(Z)-(4R,5S,6S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-6-methoxy-2,4-dimethyl-hept-2-enoic acid ethyl ester (944823-24-9) → 5-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-2,4-dimethyl-hept-2-en-1-ol (918868-28-7)

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2007.02.107

Reference yield:

(2S)-methyl 3-(tert-butyldiphenylsilyloxy)-2-methoxy-propionate (918868-38-9) → 5-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-2,4-dimethyl-hept-2-en-1-ol (918868-28-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 90 percent / DIBAL-H / CH₂Cl₂; hexane / 2.5 h / 20 °C

2.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: MgBr₂*OEt₂ / CH₂Cl₂ / 0.67 h / -21 °C

3.2: 87 percent / CH₂Cl₂ / 7 h / -60 °C

4.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

5.1: OsO₄; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H₂O / 6.5 h / 20 °C

6.1: NaIO₄ / tetrahydrofuran; H₂O / 3 h / 20 °C

7.1: 18-crown-6; KHMDS / tetrahydrofuran; toluene / 0.5 h / 0 °C

7.2: 4.77 g / tetrahydrofuran; toluene / 18 h / -78 °C

8.1: 94 percent / DIBAL-H / CH₂Cl₂; hexane / 2 h / 20 °C

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; magnesium bromide; In tetrahydrofuran; hexane; dichloromethane; water; toluene; tert-butyl alcohol; 2.1: Swern oxidation / 7.2: Still-Gennari olefination;

DOI:10.1016/j.tet.2007.02.107

Reference yield:

(2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-methoxy-4-methyl-hex-5-en-3-ol (848035-35-8) → 5-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-2,4-dimethyl-hept-2-en-1-ol (918868-28-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

2.1: OsO₄; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H₂O / 6.5 h / 20 °C

3.1: NaIO₄ / tetrahydrofuran; H₂O / 3 h / 20 °C

4.1: 18-crown-6; KHMDS / tetrahydrofuran; toluene / 0.5 h / 0 °C

4.2: 4.77 g / tetrahydrofuran; toluene / 18 h / -78 °C

5.1: 94 percent / DIBAL-H / CH₂Cl₂; hexane / 2 h / 20 °C

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; hexane; dichloromethane; water; toluene; tert-butyl alcohol; 4.2: Still-Gennari olefination;

DOI:10.1016/j.tet.2007.02.107

upstream raw materials:

C₃₈H₆₆O₄Si₃

(Z)-(4R,5S,6S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-6-methoxy-2,4-dimethyl-hept-2-enoic acid ethyl ester

(2S)-methyl 3-(tert-butyldiphenylsilyloxy)-2-methoxy-propionate

(2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-methoxy-4-methyl-hex-5-en-3-ol

Downstream raw materials:

5-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-2,4-dimethyl-hept-2-enal

C₃₉H₆₀O₅Si₂

8-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-9-methoxy-3,5,7-trimethyl-deca-1,5-dien-4-ol

7-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-8-methoxy-2,4,6-trimethyl-3-triethylsilanyloxy-non-4-enal