1-(S)-chloro-2-phenylethylboronic acid (1S,2S,3R,5S)-(+)-pinane-2,3-glycol ester

Base Information

Chemical Name:1-(S)-chloro-2-phenylethylboronic acid (1S,2S,3R,5S)-(+)-pinane-2,3-glycol ester
CAS No.:78902-03-1
Molecular Formula:C₁₈H₂₄BClO₂
Molecular Weight:318.651
Hs Code.:

Synonyms:1-(S)-chloro-2-phenylethylboronic acid (1S,2S,3R,5S)-(+)-pinane-2,3-glycol ester

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Chemical Property of 1-(S)-chloro-2-phenylethylboronic acid (1S,2S,3R,5S)-(+)-pinane-2,3-glycol ester

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Technology Process of 1-(S)-chloro-2-phenylethylboronic acid (1S,2S,3R,5S)-(+)-pinane-2,3-glycol ester

There total 8 articles about 1-(S)-chloro-2-phenylethylboronic acid (1S,2S,3R,5S)-(+)-pinane-2,3-glycol 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: 92.0%

: 75-09-2
dichloromethane

: 78922-83-5
(1-phenylmethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester

: 78902-03-1
1-(S)-chloro-2-phenylethylboronic acid (1S,2S,3R,5S)-(+)-pinane-2,3-glycol ester

Guidance literature:: With n-butyllithium; zinc(II) chloride; In tetrahydrofuran; (N2); stirring (-100°C, 10 min), ZnCl2 addn., stirring (20°C, 24 h); rot. evapn. (30°C), recrystn. (EtOH);
DOI:10.1021/ja952816j

Reference yield:

: 1589-82-8
phenylmagnesium bromide

: 87249-60-3
(3aS,4S,6S,7aR)-2-(dichloromethyl)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole

: 78902-03-1
1-(S)-chloro-2-phenylethylboronic acid (1S,2S,3R,5S)-(+)-pinane-2,3-glycol ester

Guidance literature:: With zinc(II) chloride; In diethyl ether; at -78 - 20 ℃; Inert atmosphere;
DOI:10.1021/jm9005093

Reference yield:

: 18680-27-8
pinanediol

: 78902-03-1
1-(S)-chloro-2-phenylethylboronic acid (1S,2S,3R,5S)-(+)-pinane-2,3-glycol ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 89 percent / MgSO₄ / diethyl ether

2.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -100 °C

2.2: ZnCl₂ / tetrahydrofuran; hexane / -100 - 20 °C

With n-butyllithium; magnesium sulfate; In tetrahydrofuran; diethyl ether; hexane;
DOI:10.1021/jo034837z