(2S,1'S)-tert-butyl(dimethyl)(2-(1'-(3''-fluorophenyl)allyloxy)-but-3-enyloxy)silane

Base Information

• Chemical Name: (2S,1'S)-tert-butyl(dimethyl)(2-(1'-(3''-fluorophenyl)allyloxy)-but-3-enyloxy)silane
• CAS No.: 1332506-73-6
• Molecular Formula: C₁₉H₂₉FO₂Si
• Molecular Weight: 336.522
• Mol file: 1332506-73-6.mol

Synonyms:(2S,1'S)-tert-butyl(dimethyl)(2-(1'-(3''-fluorophenyl)allyloxy)-but-3-enyloxy)silane

Chemical Property of (2S,1'S)-tert-butyl(dimethyl)(2-(1'-(3''-fluorophenyl)allyloxy)-but-3-enyloxy)silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,1'S)-tert-butyl(dimethyl)(2-(1'-(3''-fluorophenyl)allyloxy)-but-3-enyloxy)silane

There total 2 articles about (2S,1'S)-tert-butyl(dimethyl)(2-(1'-(3''-fluorophenyl)allyloxy)-but-3-enyloxy)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: 78.0%

(S)-(-)-1-(3'-fluorophenyl)prop-2-en-1-yl tert-butyl carbonate (1073277-42-5) + (S)-1-(tert-butyl-dimethyl-silanyloxy)-but-3-en-2-ol → (2S,1'S)-tert-butyl(dimethyl)(2-(1'-(3''-fluorophenyl)allyloxy)-but-3-enyloxy)silane (1332506-73-6)

Guidance literature:

(S)-1-(tert-butyl-dimethyl-silanyloxy)-but-3-en-2-ol; With n-butyllithium; In tetrahydrofuran; pentane; at 0 ℃; for 0.25h; Inert atmosphere;

With copper(l) iodide; In tetrahydrofuran; pentane; at 20 ℃; for 0.5h; Inert atmosphere;

(S)-(-)-1-(3'-fluorophenyl)prop-2-en-1-yl tert-butyl carbonate; With bis(1,5-cyclooctadiene)diiridium(I) dichloride; In tetrahydrofuran; pentane; at 0 - 20 ℃; for 16h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/jo201110z

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2S,1'S)-tert-butyl(dimethyl)(2-(1'-(3''-fluorophenyl)allyloxy)-but-3-enyloxy)silane (1332506-73-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dmap; triethylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; pentane / 0.25 h / 0 °C / Inert atmosphere

2.2: 0.5 h / 20 °C / Inert atmosphere

2.3: 16 h / 0 - 20 °C / Inert atmosphere

With dmap; n-butyllithium; triethylamine; In tetrahydrofuran; pentane;

DOI:10.1021/jo201110z

Reference yield: 95.0%

(2S,1'S)-tert-butyl(dimethyl)(2-(1'-(3''-fluorophenyl)allyloxy)-but-3-enyloxy)silane (1332506-73-6) → (-)-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-1',2',3'-trideoxy-1'-(3-fluorophenyl)-α-D-ribofuranose (1332506-82-7)

Guidance literature:

With Grubbs catalyst first generation; In dichloromethane; at 40 ℃; for 5h; Inert atmosphere;

DOI:10.1021/jo201110z

upstream raw materials:

(S)-(-)-1-(3'-fluorophenyl)prop-2-en-1-yl tert-butyl carbonate

tert-butyldimethylsilyl chloride

Downstream raw materials:

(-)-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-1',2',3'-trideoxy-1'-(3-fluorophenyl)-α-D-ribofuranose

(-)-2',3'-didehydro-1',2',3'-trideoxy-1'-(3-fluorophenyl)-α-D-ribofuranose