(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
• Mol file: 76110-79-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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%

(dichloromethyl)lithium (2146-67-0) + (3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole (76110-78-6) → (+)-pinanediol (αR)-α-chlorobenzylboronate (85922-61-8) + (S)-(chloro(phenyl)methyl)boronic acid boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester (76110-79-7)

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:

dichloromethane (75-09-2) + (3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole (76110-78-6) → (S)-(chloro(phenyl)methyl)boronic acid boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester (76110-79-7)

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:

pinanediol (18680-27-8) → (S)-(chloro(phenyl)methyl)boronic acid boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester (76110-79-7)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / -100 - 25 °C

In tetrahydrofuran;

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

upstream raw materials:

dichloromethane

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

(dichloromethyl)lithium

pinanediol

Downstream raw materials:

(+)-pinanediol (S)-1-phenylethane-1-boronate

(+)-pinanediol (αR)-α-chlorobenzylboronate

(+)-pinanediol (1R)-1-(2-thienylacetylamino)-1-phenylmethylboronate

(R)-(1-amino-1-phenylmethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester hydrochloride salt