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

Base Information

• Chemical Name: (-)-(1S)-1-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinylcyclopropyl]prop-2-en-1-ol
• CAS No.: 917483-17-1
• Molecular Formula: C₂₅H₃₂O₂Si
• Molecular Weight: 392.613
• Mol file: 917483-17-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (-)-(1S)-1-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinylcyclopropyl]prop-2-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: 48.0%

(1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinylcyclopropanecarbaldehyde (917483-15-9) + vinyl magnesium bromide (1826-67-1) → (-)-(1R)-1-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinylcyclopropyl]prop-2-en-1-ol (917483-16-0) + (-)-(1S)-1-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinylcyclopropyl]prop-2-en-1-ol (917483-17-1)

Guidance literature:

In tetrahydrofuran; at -78 ℃;

DOI:10.1080/15257770701615599

Reference yield:

(1S,5R)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-oxa-bicyclo[3.1.0]hexan-2-one → (-)-(1S)-1-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinylcyclopropyl]prop-2-en-1-ol (917483-17-1)

Guidance literature:

Multi-step reaction with 4 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

4.1: tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

4.2: 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 / 4.1: Grignard reaction / 4.2: Grignard reaction;

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) → (-)-(1S)-1-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinylcyclopropyl]prop-2-en-1-ol (917483-17-1)

Guidance literature:

Multi-step reaction with 3 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

3.1: tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

3.2: 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 / 3.1: Grignard reaction / 3.2: Grignard reaction;

DOI:10.1016/j.bmc.2011.05.026

upstream raw materials:

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

vinyl magnesium bromide

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

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

Downstream raw materials:

(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

(1'R,2'R,5'S)-1-{5-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]bicyclo[3.1.0]hex-3-en-2-yl}-5-methyl-3-(phenylcarbonyl)-1,3-dihydropyrimidine-2,4-dione

3-benzoyl-1-[(1R,2R,5S)-5-(tert-butyl-diphenylsilanyloxymethyl)bicyclo[3.1.0]hex-3-en-2-yl]pyrimidine-2,4(1H,3H)-dione