(1S,4R)-4-[3-(tert-butyldiphenylsiloxy)propyl]-4-vinyl-2-cyclohexen-1-ol

Base Information

Chemical Name:(1S,4R)-4-[3-(tert-butyldiphenylsiloxy)propyl]-4-vinyl-2-cyclohexen-1-ol
CAS No.:503000-26-8
Molecular Formula:C₂₇H₃₆O₂Si
Molecular Weight:420.667
Hs Code.:

Synonyms:(1S,4R)-4-[3-(tert-butyldiphenylsiloxy)propyl]-4-vinyl-2-cyclohexen-1-ol

Suppliers and Price of (1S,4R)-4-[3-(tert-butyldiphenylsiloxy)propyl]-4-vinyl-2-cyclohexen-1-ol

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Chemical Property of (1S,4R)-4-[3-(tert-butyldiphenylsiloxy)propyl]-4-vinyl-2-cyclohexen-1-ol

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Technology Process of (1S,4R)-4-[3-(tert-butyldiphenylsiloxy)propyl]-4-vinyl-2-cyclohexen-1-ol

There total 24 articles about (1S,4R)-4-[3-(tert-butyldiphenylsiloxy)propyl]-4-vinyl-2-cyclohexen-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: 87.0%

: 503000-40-6
C₂₇H₃₆SiO₂C₂H₄SiC₃H₈

: (1S,4S)-4-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-4-vinyl-cyclohex-2-enol

: 503000-26-8
(1S,4R)-4-[3-(tert-butyldiphenylsiloxy)propyl]-4-vinyl-2-cyclohexen-1-ol

Guidance literature:: C₂₇H₃₆SiO₂C₂H₄SiC₃H₈; With Grubbs catalyst first generation; In dichloromethane; at 20 ℃; for 48h;

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 0.5h; Further stages.; Acid hydrolysis;
DOI:10.1021/ol034020s

Reference yield:

: 503000-50-8
6-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-6-vinyl-octa-2,7-dienoic acid ethyl ester

: 503000-26-8
(1S,4R)-4-[3-(tert-butyldiphenylsiloxy)propyl]-4-vinyl-2-cyclohexen-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 100 percent / DIBAl-H / tetrahydrofuran; hexane / 0.5 h / 0 °C

2.1: 92 percent / L-(+)-DIPT; molecular sieves 4 Angstroem; TBHP / Ti(i-PrO)4 / CH₂Cl₂ / -25 - 20 °C

3.1: 95 percent / triphenylphosphine; I₂; imidazole / benzene / 0.5 h / 20 °C

4.1: 96 percent / Zn; acetic acid / 0.5 h / 50 °C

5.1: 98 percent / Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

6.1: (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 48 h / 20 °C

6.2: 87 percent / aq. HCl / tetrahydrofuran / 0.5 h / 20 °C / Acid hydrolysis

With 1H-imidazole; tert.-butylhydroperoxide; Grubbs catalyst first generation; L-(+)-diisopropyl tartrate; 4 A molecular sieve; iodine; diisobutylaluminium hydride; acetic acid; triethylamine; triphenylphosphine; zinc; titanium(IV) isopropylate; In tetrahydrofuran; hexane; dichloromethane; benzene; 2.1: Katsuki-Sharpless asymmetric epoxidation;
DOI:10.1021/ol034020s

Reference yield:

: 503000-47-3
1-[3-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-6-(tert-butyl-diphenyl-silanyloxy)-3-vinyl-hexylselanyl]-2-nitro-benzene

: 503000-26-8
(1S,4R)-4-[3-(tert-butyldiphenylsiloxy)propyl]-4-vinyl-2-cyclohexen-1-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 91 percent / H₂O₂ / tetrahydrofuran / 1 h / 20 °C

2.1: 100 percent / aq. HCl / ethanol / 2 h / 20 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

4.1: 89 percent / benzene / 5 h / Heating

5.1: 100 percent / DIBAl-H / tetrahydrofuran; hexane / 0.5 h / 0 °C

6.1: 92 percent / L-(+)-DIPT; molecular sieves 4 Angstroem; TBHP / Ti(i-PrO)4 / CH₂Cl₂ / -25 - 20 °C

7.1: 95 percent / triphenylphosphine; I₂; imidazole / benzene / 0.5 h / 20 °C

8.1: 96 percent / Zn; acetic acid / 0.5 h / 50 °C

9.1: 98 percent / Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

10.1: (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 48 h / 20 °C

10.2: 87 percent / aq. HCl / tetrahydrofuran / 0.5 h / 20 °C / Acid hydrolysis

With 1H-imidazole; hydrogenchloride; tert.-butylhydroperoxide; Grubbs catalyst first generation; oxalyl dichloride; L-(+)-diisopropyl tartrate; 4 A molecular sieve; dihydrogen peroxide; iodine; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc; titanium(IV) isopropylate; In tetrahydrofuran; ethanol; hexane; dichloromethane; benzene; 4.1: Wittig reaction / 6.1: Katsuki-Sharpless asymmetric epoxidation;
DOI:10.1021/ol034020s