(S)-2-(2-phenylbut-3-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: (S)-2-(2-phenylbut-3-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 1201898-76-1
• Molecular Formula: C₁₆H₂₃BO₂
• Molecular Weight: 258.168
• Mol file: 1201898-76-1.mol

Synonyms:(S)-2-(2-phenylbut-3-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of (S)-2-(2-phenylbut-3-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-(2-phenylbut-3-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 2 articles about (S)-2-(2-phenylbut-3-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 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: 89.0%

pinacol vinylboronate (75927-49-0) + (S)-(-)-1-phenylethyl N,N-diisopropylcarbamate (133038-74-1) → (S)-2-(2-phenylbut-3-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1201898-76-1)

Guidance literature:

(S)-(-)-1-phenylethyl N,N-diisopropylcarbamate; With sec.-butyllithium; In diethyl ether; hexane; cyclohexane; at -75 - -70 ℃; for 0.416667h; Inert atmosphere;

pinacol vinylboronate; In diethyl ether; hexane; cyclohexane; at -70 ℃; for 4.75h; Inert atmosphere;

DOI:10.1016/j.tet.2009.10.002

Reference yield:

(E)-methyl 3-phenylbut-2-enyl carbonate (157397-76-7) + bis(pinacol)diborane (73183-34-3) → (S)-2-(2-phenylbut-3-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1201898-76-1) + C16H23BO2

Guidance literature:

With (C₆H₅)2C₃N₂H₃((CH₃)3C₆H₂)C₆H₄SO₃; sodium methylate; copper(II) bis(trifluoromethanesulfonate); In 1,2-dimethoxyethane; at 22 ℃; for 24h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja104254d

Reference yield: 98.0%

(S)-2-(2-phenylbut-3-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1201898-76-1) → potassium (S)-(2-phenylbut-3-en-2-yl)trifluoroborate

Guidance literature:

With potassium hydrogenfluoride; water; In methanol; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2009.10.002

upstream raw materials:

pinacol vinylboronate

(S)-(-)-1-phenylethyl N,N-diisopropylcarbamate

(E)-methyl 3-phenylbut-2-enyl carbonate

bis(pinacol)diborane