1-(tert-butyl-diphenyl-silanyloxy)-2-methyl-hept-5-yn-3-ol

Base Information

• Chemical Name: 1-(tert-butyl-diphenyl-silanyloxy)-2-methyl-hept-5-yn-3-ol
• CAS No.: 347884-43-9
• Molecular Formula: C₂₄H₃₂O₂Si
• Molecular Weight: 380.602
• Mol file: 347884-43-9.mol

Synonyms:1-(tert-butyl-diphenyl-silanyloxy)-2-methyl-hept-5-yn-3-ol

Chemical Property of 1-(tert-butyl-diphenyl-silanyloxy)-2-methyl-hept-5-yn-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(tert-butyl-diphenyl-silanyloxy)-2-methyl-hept-5-yn-3-ol

There total 2 articles about 1-(tert-butyl-diphenyl-silanyloxy)-2-methyl-hept-5-yn-3-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: 92.0%

(2S,3RS)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-3,4-epoxybutane (223437-33-0) + prop-1-yne (74-99-7) → 1-(tert-butyl-diphenyl-silanyloxy)-2-methyl-hept-5-yn-3-ol (347884-43-9)

Guidance literature:

prop-1-yne; With n-butyllithium; In tetrahydrofuran; Petroleum ether; at -78 ℃; for 0.166667h;

(2S,3RS)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-3,4-epoxybutane; With boron trifluoride diethyl etherate; In tetrahydrofuran; Petroleum ether; at -78 ℃; for 2h; Further stages.;

DOI:10.1021/ja0105414

Reference yield:

(R)-4-[(tert-butyldiphenylsilyl)oxy]-3-methylbut-1-ene (132117-93-2) → 1-(tert-butyl-diphenyl-silanyloxy)-2-methyl-hept-5-yn-3-ol (347884-43-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 80 percent / m-CPBA / CH₂Cl₂ / 12 h / 20 °C

2.1: n-BuLi / tetrahydrofuran; petroleum ether / 0.17 h / -78 °C

2.2: 92 percent / BF₃*Et₂O / tetrahydrofuran; petroleum ether / 2 h / -78 °C

With n-butyllithium; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; Petroleum ether;

DOI:10.1021/ja0105414

Reference yield:

1-(tert-butyl-diphenyl-silanyloxy)-2-methyl-hept-5-yn-3-ol (347884-43-9) → 3,3,3-trifluoro-2-methoxy-2-phenyl-propionic acid 6-[5,7-dimethyl-12-oxo-8-(3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-oxacyclododec-4-en-2-yl]-2,4-dimethyl-1-[2-(3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-propyl]-hept-3-enyl ester

Guidance literature:

Multi-step reaction with 17 steps

1.1: 73 percent / TBAF / tetrahydrofuran / 12 h

2.1: TsOH; MgSO₄ / benzene / 72 h

3.1: Cp₂ZrHCl / tetrahydrofuran / 1 h / 50 °C

3.2: 62 percent / I₂ / tetrahydrofuran / 0.5 h / 20 °C

4.1: t-BuLi; ZnCl₂ / tetrahydrofuran; pentane / 0.5 h / -78 - 20 °C

4.2: 60 percent / Pd(Ph₃P)4 / tetrahydrofuran; pentane / 12 h / 20 °C

5.1: 77 percent / aq. TFA / CH₂Cl₂ / 2 h

6.1: 99 percent / pyridine

7.1: 91 percent / imidazole / CH₂Cl₂ / 1 h

8.1: 98 percent / DiBAL-H / CH₂Cl₂; petroleum ether / 1 h / -78 °C

9.1: 91 percent / I₂; Ph₃P; imidazole / diethyl ether; acetonitrile / 12 h

10.1: t-BuLi; ZnCl₂ / tetrahydrofuran; pentane / 30 h / -78 - 20 °C

10.2: 50 percent / Pd(Ph₃P)4 / tetrahydrofuran; pentane / 12 h / 20 °C

11.1: 72 percent / HF*pyridine; pyridine / tetrahydrofuran / 2 h

12.1: 95 percent / TEMPO; NCS; Bu₄NCl / CH₂Cl₂ / 1 h / pH 8.6

13.1: 94 percent / aq.NaClO₂; Na₂HPO₄; m-(MeO)-C₆H₄ / dimethylsulfoxide; 2-methyl-propan-2-ol / 1 h / pH 4.5

14.1: Cl₃C₆H₂COCl; i-Pr₂NEt / benzene / 1 h

14.2: 70 percent / DMAP / benzene / 6 h

15.1: 62 percent / aq. TFA / CH₂Cl₂ / 3 h

16.1: 77 percent / HF*pyridine / acetonitrile / 1.5 h

With pyridine; 1H-imidazole; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; disodium hydrogenphosphate; N-chloro-succinimide; Schwartz's reagent; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; iodine; tert.-butyl lithium; diisobutylaluminium hydride; magnesium sulfate; toluene-4-sulfonic acid; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; zinc(II) chloride; 1,3-Dimethoxybenzene; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; acetonitrile; Petroleum ether; tert-butyl alcohol; pentane; benzene; 14.2: Yamaguchi macrolactonization;

DOI:10.1021/ja0105414

upstream raw materials:

(2S,3RS)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-3,4-epoxybutane

prop-1-yne

(R)-4-[(tert-butyldiphenylsilyl)oxy]-3-methylbut-1-ene