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

Base Information

Chemical Name:(Z)-(4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-4,6-dimethyl-hept-2-enoic acid methyl ester
CAS No.:475051-59-3
Molecular Formula:C₃₂H₅₀O₄Si₂
Molecular Weight:554.918
Hs Code.:

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

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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-enoic acid methyl ester

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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-enoic acid methyl ester

There total 17 articles about (Z)-(4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-4,6-dimethyl-hept-2-enoic acid methyl 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: 95.0%

: 88738-78-7
bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate

: 475051-47-9
(2R,3R,4S)-3-(tert-butyldimethylsiloxy)-5-(tert-butyldiphenylsiloxy)-2,4-dimethylpentanal

: 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

Guidance literature:: With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 15h;
DOI:10.1016/S0040-4039(02)01389-8

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 7 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

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

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

Guidance literature:: Multi-step reaction with 6 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

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