(S)-(chloro(phenyl)methyl)boronic acid boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester

Base Information

Chemical Name:(S)-(chloro(phenyl)methyl)boronic acid boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester
CAS No.:76110-79-7
Molecular Formula:C₁₇H₂₂BClO₂
Molecular Weight:304.624
Hs Code.:

Synonyms:(S)-(chloro(phenyl)methyl)boronic acid boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester

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Chemical Property of (S)-(chloro(phenyl)methyl)boronic acid boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester

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Technology Process of (S)-(chloro(phenyl)methyl)boronic acid boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester

There total 6 articles about (S)-(chloro(phenyl)methyl)boronic acid 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: 83.6%

: 2146-67-0
(dichloromethyl)lithium

: 76110-78-6
(3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole

: 85922-61-8
(+)-pinanediol (αR)-α-chlorobenzylboronate

: 76110-79-7
(S)-(chloro(phenyl)methyl)boronic acid boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester

Guidance literature:: With zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; LiCH2Cl in THF/CH2Cl2 was treated with boronate in ether; to the slurry at -100°C was added ZnCl2; warming to -30 - -25°C for 45 min; evapn. in vac. at -10°C, residue was treated with petroleum ether followed by ice water; chromy. on silica (petroleum ether); crystn. from hexane: elem. anal.;

Reference yield:

: 75-09-2
dichloromethane

: 76110-78-6
(3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole

: 76110-79-7
(S)-(chloro(phenyl)methyl)boronic acid boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester

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

(3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole; In tetrahydrofuran; hexane; at -100 - 20 ℃; Further stages.;
DOI:10.1021/ja0288338

Reference yield:

: 18680-27-8
pinanediol

: 76110-79-7
(S)-(chloro(phenyl)methyl)boronic acid boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester

Guidance literature:: Multi-step reaction with 2 steps

1: tetrahydrofuran / -100 - 25 °C

In tetrahydrofuran;
DOI:10.1016/S0960-894X(02)00682-0