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

Base Information

Chemical Name:(Z)-(4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-4,6-dimethyl-hept-2-en-1-ol
CAS No.:475051-60-6
Molecular Formula:C₃₁H₅₀O₃Si₂
Molecular Weight:526.907
Hs Code.:

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

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

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

There total 18 articles about (Z)-(4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-4,6-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: 90.0%

: 475051-59-3
(Z)-(4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-4,6-dimethyl-hept-2-enoic acid methyl ester

: 475051-60-6
(Z)-(4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-4,6-dimethyl-hept-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 3h;
DOI:10.1016/S0040-4039(02)01389-8 DOI:10.1021/jo034901c

Reference yield:

: 374896-36-3
ethyl (2R,3S,4S)-2-bromo-5-(tert-butyldimethylsiloxy)-3-hydroxy-2,4-dimethylpentanoate

: 475051-60-6
(Z)-(4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-4,6-dimethyl-hept-2-en-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 80 percent / Mg; ethelene dibromide; Bu₃SnH / Et₃B / CH₂Cl₂; diethyl ether / 2 h / 0 °C

2: 87 percent / 2,6-lutidine / 1 h / 20 °C

3: 80 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

4: 92 percent / imidazole / CH₂Cl₂ / 1 h / 20 °C

5: 90 percent / pyridinium p-toluenesulfonate / methanol / 20 h / 20 °C

6: 87 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

7: 95 percent / 18-crown-6; KHMDS / tetrahydrofuran / 15 h / -78 °C

8: 90 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; oxalyl dichloride; 18-crown-6 ether; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; magnesium; dimethyl sulfoxide; ethylene dibromide; triethylamine; triethyl borane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 6: Swern oxidation / 7: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo034901c

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 475051-60-6
(Z)-(4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-4,6-dimethyl-hept-2-en-1-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 87 percent / 2,6-lutidine / 1 h / 20 °C

2: 80 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

3: 92 percent / imidazole / CH₂Cl₂ / 1 h / 20 °C

4: 90 percent / pyridinium p-toluenesulfonate / methanol / 20 h / 20 °C

5: 87 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

6: 95 percent / 18-crown-6; KHMDS / tetrahydrofuran / 15 h / -78 °C

7: 90 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; oxalyl dichloride; 18-crown-6 ether; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 5: Swern oxidation / 6: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo034901c