((S)-1-Bromomethyl-2-(S)-oxiranyl-ethoxy)-tert-butyl-diphenyl-silane

Base Information

• Chemical Name: ((S)-1-Bromomethyl-2-(S)-oxiranyl-ethoxy)-tert-butyl-diphenyl-silane
• CAS No.: 183559-06-0
• Molecular Formula: C₂₁H₂₇BrO₂Si
• Molecular Weight: 419.434
• Mol file: 183559-06-0.mol

Synonyms:((S)-1-Bromomethyl-2-(S)-oxiranyl-ethoxy)-tert-butyl-diphenyl-silane

Chemical Property of ((S)-1-Bromomethyl-2-(S)-oxiranyl-ethoxy)-tert-butyl-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((S)-1-Bromomethyl-2-(S)-oxiranyl-ethoxy)-tert-butyl-diphenyl-silane

There total 3 articles about ((S)-1-Bromomethyl-2-(S)-oxiranyl-ethoxy)-tert-butyl-diphenyl-silane 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: 56.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (2S,4S)-1,5-Dibromo-pentane-2,4-diol (183559-05-9) → ((S)-1-Bromomethyl-2-(S)-oxiranyl-ethoxy)-tert-butyl-diphenyl-silane (183559-06-0)

Guidance literature:

With pyridine; 1H-imidazole; potassium hydroxide; at -10 ℃;

DOI:10.1016/0040-4039(96)01700-5

Reference yield:

(2S,4S)-1,5-dichloro-2,4-pentanediol (136030-29-0) → ((S)-1-Bromomethyl-2-(S)-oxiranyl-ethoxy)-tert-butyl-diphenyl-silane (183559-06-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / 1.) KOH; 2.) Li₂NiBr₄ / 1.) ether; 2.) THF, r.t., 5 h

2: 56 percent / 1.) imidazole, pyridine; 2.) KOH / -10 °C

With pyridine; 1H-imidazole; potassium hydroxide; dilithium tetrabromonickelate(II);

DOI:10.1016/0040-4039(96)01700-5

Reference yield:

acetylacetone (123-54-6,81235-32-7) → ((S)-1-Bromomethyl-2-(S)-oxiranyl-ethoxy)-tert-butyl-diphenyl-silane (183559-06-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) AlCl₃, ClCH₂COCl, Cu(OAc)2; 2.) 10percent H₂SO₄; 3.) <((R)BINAP)RuCl₂>2Et₃N, H₂ / 1.) CH₂Cl₂, PhNO₂, 60 deg C, 4 h; 2.) Et₂O; 3.) 1200 psi, 102 deg C

2: 90 percent / 1.) KOH; 2.) Li₂NiBr₄ / 1.) ether; 2.) THF, r.t., 5 h

3: 56 percent / 1.) imidazole, pyridine; 2.) KOH / -10 °C

With pyridine; 1H-imidazole; potassium hydroxide; aluminium trichloride; copper diacetate; [(R)-BINAP RuCl₂]2NEt₃; dilithium tetrabromonickelate(II); sulfuric acid; hydrogen; chloroacetyl chloride;

DOI:10.1016/0040-4039(96)01700-5

upstream raw materials:

tert-butylchlorodiphenylsilane

(2S,4S)-1,5-Dibromo-pentane-2,4-diol

(2S,4S)-1,5-dichloro-2,4-pentanediol

acetylacetone

Downstream raw materials:

1-[(1S,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-bicyclo[3.1.0]hex-1-yl]-2-[(1R,3aR,7aR)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-ethanol

1-[(1S,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-bicyclo[3.1.0]hex-1-yl]-2-[(1R,3aS,7aR)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-ethanol

(1R,3aS,7aR)-4-[(1S,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-bicyclo[3.1.0]hex-1-ylethynyl]-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-4-ol

(1R,3aR,7aR)-4-[(1S,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-bicyclo[3.1.0]hex-1-ylethynyl]-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-4-ol