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

Base Information

• Chemical Name: (+)-pinanediol (αR)-α-chlorobenzylboronate
• CAS No.: 85922-61-8
• Molecular Formula: C₁₇H₂₂BClO₂
• Molecular Weight: 304.624
• Mol file: 85922-61-8.mol

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

Chemical Property of (+)-pinanediol (αR)-α-chlorobenzylboronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-pinanediol (αR)-α-chlorobenzylboronate

There total 7 articles about (+)-pinanediol (αR)-α-chlorobenzylboronate 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: 67.0%

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

Guidance literature:

dichloromethane; (3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole; With lithium diisopropyl amide; In tetrahydrofuran; cyclohexane; at -20 ℃;

With zinc(II) chloride; In tetrahydrofuran; diethyl ether; cyclohexane; at -20 - 23 ℃; Further stages.;

DOI:10.1016/j.tet.2007.03.033

Reference yield:

(S)-(chloro(phenyl)methyl)boronic acid boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester (76110-79-7) → (+)-pinanediol (αR)-α-chlorobenzylboronate (85922-61-8)

Guidance literature:

With H₂O or Me₂SO or HgCl₂ or triglyme; or dibenzo-18-crown-6; lithium chloride; In tetrahydrofuran; 25°C; Kinetics;

upstream raw materials:

dichloromethane

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

pinanediol

(+)-α-pinene

Downstream raw materials:

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

Refernces

• 1、 Debaene, Fran?ois,Da Silva, Julien A.,Pianowski, Zbigniew,Duran, Fernando J.,Winssinger, Nicolas. "Expanding the scope of PNA-encoded libraries: divergent synthesis of libraries targeting cysteine, serine and metallo-proteases as well as tyrosine phosphatases". . p. 6577 - 6586. Retrieved 2008/02/05.
• 2、 Matteson, Donald S.,Erdik, Ender. "Epimerization of α-chloro boronic esters by lithium and zinc chlorides". . p. 1083 - 1088. Retrieved 2008/10/08.