[2(1'S),4R,5R]-2-[3-[[(1,1-dimethylethyl)oxy]carbonyl]-1-chloropropyl]-4,5-dicyclohexyl-1,3,2-dioxaborolane

Base Information

Chemical Name:[2(1'S),4R,5R]-2-[3-[[(1,1-dimethylethyl)oxy]carbonyl]-1-chloropropyl]-4,5-dicyclohexyl-1,3,2-dioxaborolane
CAS No.:325141-82-0
Molecular Formula:C₂₂H₃₈BClO₄
Molecular Weight:412.805
Hs Code.:

Synonyms:[2(1'S),4R,5R]-2-[3-[[(1,1-dimethylethyl)oxy]carbonyl]-1-chloropropyl]-4,5-dicyclohexyl-1,3,2-dioxaborolane

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Chemical Property of [2(1'S),4R,5R]-2-[3-[[(1,1-dimethylethyl)oxy]carbonyl]-1-chloropropyl]-4,5-dicyclohexyl-1,3,2-dioxaborolane

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Technology Process of [2(1'S),4R,5R]-2-[3-[[(1,1-dimethylethyl)oxy]carbonyl]-1-chloropropyl]-4,5-dicyclohexyl-1,3,2-dioxaborolane

There total 4 articles about [2(1'S),4R,5R]-2-[3-[[(1,1-dimethylethyl)oxy]carbonyl]-1-chloropropyl]-4,5-dicyclohexyl-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: 79.0%

: 2146-67-0
(dichloromethyl)lithium

: 325141-81-9
(4R,5R)-2-[2-[[(1,1-dimethylethyl)oxy]carbonyl]ethyl]-4,5-dicyclohexyl-1,3,2-dioxaborolane

: 325141-82-0
[2(1'S),4R,5R]-2-[3-[[(1,1-dimethylethyl)oxy]carbonyl]-1-chloropropyl]-4,5-dicyclohexyl-1,3,2-dioxaborolane

Guidance literature:: With zinc(II) chloride; In tetrahydrofuran; diethyl ether; at 20 - 25 ℃; for 20h;
DOI:10.1016/S0022-328X(00)00595-7

Reference yield: 79.0%

: 75-09-2
dichloromethane

: 325141-81-9
(4R,5R)-2-[2-[[(1,1-dimethylethyl)oxy]carbonyl]ethyl]-4,5-dicyclohexyl-1,3,2-dioxaborolane

: 325141-82-0
[2(1'S),4R,5R]-2-[3-[[(1,1-dimethylethyl)oxy]carbonyl]-1-chloropropyl]-4,5-dicyclohexyl-1,3,2-dioxaborolane

Guidance literature:: With n-butyllithium; zinc(II) chloride; In tetrahydrofuran; diethyl ether; (dichloromethyl)lithiym was prepared by addn. BuLi to soln. CH2Cl2 in THF stirred at -100°C, soln. dioxaborolane in THF was added, mixt. was allowed to warm to -78°C, ZnCl2 in Et2O was added and soln. was kept for 20 h at 20-25°C; react. mixt. was poured into pentane, org. phase was washed with water and concd. under vac., residue was dissolved in pentane, washed with water, dried over MgSO4, filtered, and concd.;
DOI:10.1016/S0022-328X(00)00595-7

Reference yield:

: 540-88-5
acetic acid tert-butyl ester

: 325141-82-0
[2(1'S),4R,5R]-2-[3-[[(1,1-dimethylethyl)oxy]carbonyl]-1-chloropropyl]-4,5-dicyclohexyl-1,3,2-dioxaborolane

Guidance literature:: Multi-step reaction with 3 steps

1: 92 percent / lithium diisopropylamide / tetrahydrofuran / -78 - 20 °C

2: 94 percent / diethyl ether

3: 79 percent / zinc chloride / tetrahydrofuran; diethyl ether / 20 h / 20 - 25 °C

With zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether;
DOI:10.1016/S0022-328X(00)00595-7