(2S)-(4E)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhex-4-en-1-ol

Base Information

• Chemical Name: (2S)-(4E)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhex-4-en-1-ol
• CAS No.: 343262-92-0
• Molecular Formula: C₂₄H₃₄O₂Si
• Molecular Weight: 382.618
• Mol file: 343262-92-0.mol

Synonyms:(2S)-(4E)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhex-4-en-1-ol

Chemical Property of (2S)-(4E)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhex-4-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-(4E)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhex-4-en-1-ol

There total 1 articles about (2S)-(4E)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhex-4-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: 87.0%

(S)-4-benzyl-3-[(2S)-(4E)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethyl-hex-4-enoyl]-oxazolidin-2-one (343262-67-9) → (2S)-(4E)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhex-4-en-1-ol (343262-92-0)

Guidance literature:

With methanol; lithium borohydride; In diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1021/ol015753k

Reference yield: 94.0%

(2S)-(4E)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhex-4-en-1-ol (343262-92-0) → (2S)-(4E)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethyl-hex-4-enal (343262-68-0)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1021/ol015753k

Reference yield:

(2S)-(4E)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhex-4-en-1-ol (343262-92-0) → 2,2-Dimethyl-propionic acid (2E,4Z,8E)-(1R,6S)-1-(2-benzenesulfonyl-ethyl)-10-bromo-4,6,8-trimethyl-deca-2,4,8-trienyl ester

Guidance literature:

Multi-step reaction with 13 steps

1.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 0.5 h / -78 °C

2.1: 99 percent / potassium bis(trimethylsilyl)amide; 18-crown-6 / tetrahydrofuran; toluene / 2 h / -78 °C

3.1: 98 percent / DIBAL / diethyl ether / 1.5 h / -78 - 20 °C

4.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 0.75 h / -78 °C

5.1: triphenylphosphine / CH₂Cl₂ / 0.17 h / 0 °C

5.2: 1.05 g / n-BuLi / tetrahydrofuran / 1 h / -78 °C

6.1: Cp₂Zr(H)Cl / CH₂Cl₂ / 0.17 h / 23 °C

6.2: Me₂Zn / CH₂Cl₂ / 0.25 h / -65 °C

6.3: 92 percent / CH₂Cl₂ / 1.5 h / 0 °C

7.1: 84 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.25 h / 20 °C

8.1: LiAlH₄; (-)-N-Me-ephedrine; EtNHC₆H₅ / diethyl ether / 1.5 h / -78 °C

9.1: (NH₄)6Mo₇O₂₄; H₂O₂ / aq. ethanol / 0 °C

10.1: pyridine; DMAP / CH₂Cl₂

11.1: TBAF / tetrahydrofuran

12.1: collidine / CH₂Cl₂ / 0 °C

13.1: LiBr / tetrahydrofuran

With pyridine; 2,3,5-trimethyl-pyridine; dmap; ammonium heptamolybdate; lithium aluminium tetrahydride; Schwartz's reagent; oxalyl dichloride; 18-crown-6 ether; (-)-N-methylephedrine; tetrabutyl ammonium fluoride; dihydrogen peroxide; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; N-ethyl-N-phenylamine; triethylamine; triphenylphosphine; lithium bromide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; toluene; 1.1: Swern oxidation / 7.1: Dess-Martin oxidation;

DOI:10.1021/ol015753k

upstream raw materials:

(S)-4-benzyl-3-[(2S)-(4E)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethyl-hex-4-enoyl]-oxazolidin-2-one

Downstream raw materials:

(2S)-(4E)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethyl-hex-4-enal

(2Z,6E)-(4S)-8-(tert-butyldiphenylsilanyloxy)-2,4,6-trimethylocta-2,6-dienal

(2Z,6E)-(4S)-8-(tert-butyldiphenylsilanyloxy)-2,4,6-trimethylocta-2,6-dien-1-ol

(3Z,7E)-(5S)-9-(tert-butyldiphenylsilanyloxy)-3,5,7-trimethylocta-3,7-dien-1-yne