(1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinylcyclopropanecarbaldehyde

Base Information

• Chemical Name: (1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinylcyclopropanecarbaldehyde
• CAS No.: 917483-15-9
• Molecular Formula: C₂₃H₂₈O₂Si
• Molecular Weight: 364.56
• Mol file: 917483-15-9.mol

Synonyms:(1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinylcyclopropanecarbaldehyde

Chemical Property of (1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinylcyclopropanecarbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinylcyclopropanecarbaldehyde

There total 6 articles about (1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinylcyclopropanecarbaldehyde 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: 99.0%

(1R,2S)-[2-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinylcyclopropyl]methanol (917483-14-8) → (1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinylcyclopropanecarbaldehyde (917483-15-9)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃; for 2h;

DOI:10.1039/b612537a

Reference yield:

(1S,5R)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-oxa-bicyclo[3.1.0]hexan-2-one → (1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinylcyclopropanecarbaldehyde (917483-15-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.5 h / -78 °C / Inert atmosphere

2.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

With oxalyl dichloride; potassium tert-butylate; diisobutylaluminium hydride; dimethyl sulfoxide; In tetrahydrofuran; hexane; dichloromethane; 2.2: Wittig reaction / 3.1: Swern oxidation / 3.2: Swern oxidation;

DOI:10.1016/j.bmc.2011.05.026

Reference yield:

(1S,5R)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-oxabicyclo[3.1.0]hexan-2-ol (917483-13-7) → (1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinylcyclopropanecarbaldehyde (917483-15-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

With oxalyl dichloride; potassium tert-butylate; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 1.2: Wittig reaction / 2.1: Swern oxidation / 2.2: Swern oxidation;

DOI:10.1016/j.bmc.2011.05.026

upstream raw materials:

(1R,2S)-[2-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinylcyclopropyl]methanol

(1S,5R)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-oxabicyclo[3.1.0]hexan-2-ol

diethyl malonate

ethyl (1S,5R)-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate

Downstream raw materials:

(-)-(1R)-1-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinylcyclopropyl]prop-2-en-1-ol

(-)-(1S)-1-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinylcyclopropyl]prop-2-en-1-ol

(1R,2S,5S)-5-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]bicyclo[3.1.0]hex-3-en-2-ol

1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-bicyclo[3.1.0]hex-3-en-2-yl]-5-methyl-1H-pyrimidine-2,4-dione