(S)-(1-chloro-2-(4'-methoxyphenyl)ethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester

Base Information

Chemical Name:(S)-(1-chloro-2-(4'-methoxyphenyl)ethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester
CAS No.:1158974-83-4
Molecular Formula:C₁₉H₂₆BClO₃
Molecular Weight:348.678
Hs Code.:

Synonyms:(S)-(1-chloro-2-(4'-methoxyphenyl)ethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester

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Chemical Property of (S)-(1-chloro-2-(4'-methoxyphenyl)ethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester

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Technology Process of (S)-(1-chloro-2-(4'-methoxyphenyl)ethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester

There total 4 articles about (S)-(1-chloro-2-(4'-methoxyphenyl)ethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester 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: 98.0%

: 75-09-2
dichloromethane

: 243145-80-4
(3aS,4S,6S,7aR)-2-(4-methoxybenzyl)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole

: 1158974-83-4
(S)-(1-chloro-2-(4'-methoxyphenyl)ethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester

: (3aS,4S,6S,7aR)-2-((R)-1-chloro-2-(4-methoxyphenyl)ethyl)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole

Guidance literature:: dichloromethane; With n-butyllithium; In tetrahydrofuran; hexane; at -100 ℃; for 0.5h;

(3aS,4S,6S,7aR)-2-(4-methoxybenzyl)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole; With zinc(II) chloride; In tetrahydrofuran; diethyl ether; hexane; at -100 - 20 ℃; optical yield given as %de; diastereoselective reaction;
DOI:10.1016/j.bmcl.2009.02.117

Reference yield:

: 75-09-2
dichloromethane

: 243145-80-4
(3aS,4S,6S,7aR)-2-(4-methoxybenzyl)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole

: 1158974-83-4
(S)-(1-chloro-2-(4'-methoxyphenyl)ethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester

Guidance literature:: dichloromethane; With n-butyllithium; In tetrahydrofuran; hexane; at -100 ℃; for 0.666667h; Inert atmosphere;

(3aS,4S,6S,7aR)-2-(4-methoxybenzyl)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole; In tetrahydrofuran; hexane; at -100 ℃; for 0.583333h; Inert atmosphere;

With zinc(II) chloride; In tetrahydrofuran; hexane; at -100 - 20 ℃; Inert atmosphere;
DOI:10.1021/acs.jmedchem.9b00735

Reference yield:

: 475250-52-3
2-[(4-methoxyphenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 1158974-83-4
(S)-(1-chloro-2-(4'-methoxyphenyl)ethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: diethyl ether / 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -100 °C / Inert atmosphere

2.2: 0.58 h / -100 °C / Inert atmosphere

2.3: -100 - 20 °C / Inert atmosphere

With n-butyllithium; In tetrahydrofuran; diethyl ether; hexane; 2.1: |Matteson Homologation / 2.2: |Matteson Homologation / 2.3: |Matteson Homologation;
DOI:10.1021/acs.jmedchem.9b00735