(R)-BoroPhe-(+)-Pinanediol-HCl

Base Information

• Chemical Name: (R)-BoroPhe-(+)-Pinanediol-HCl
• CAS No.: 178455-03-3
• Molecular Formula: C₁₈H₂₆BNO₂*ClH
• Molecular Weight: 335.682
• Mol file: 178455-03-3.mol

Synonyms:4,6-Methano-1,3,2-benzodioxaborole-2-methanamine,hexahydro-3a,5,5-trimethyl-a-(phenylmethyl)-, hydrochloride, [3aS-[2(S*),3aa,4b,6b,7aa]]- (9CI)

Chemical Property of (R)-BoroPhe-(+)-Pinanediol-HCl

Chemical Property:

• PSA: 44.48000
• LogP: 4.74610

Purity/Quality:

99%min ^*data from raw suppliers

(R)-BoroPhe-(+)-Pinanediol-HCl 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R)-BoroPhe-(+)-Pinanediol-HCl

There total 17 articles about (R)-BoroPhe-(+)-Pinanediol-HCl 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:

1-(S)-chloro-2-phenylethylboronic acid (1S,2S,3R,5S)-(+)-pinane-2,3-glycol ester (78902-03-1) → (R)-2-phenyl-1-((3a5,45,65,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)ethanamine hydrochloride (178455-03-3)

Guidance literature:

1-(S)-chloro-2-phenylethylboronic acid (1S,2S,3R,5S)-(+)-pinane-2,3-glycol ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20 ℃;

With hydrogenchloride; In 1,4-dioxane; diethyl ether; at -60 ℃; for 3h;

Reference yield:

C24H42BNO2Si2 → (+)-pinanediol 1-amino-2-phenylethyl-1-boronate hydrochloride (178455-03-3)

Guidance literature:

With hydrogenchloride; In diethyl ether; Petroleum ether; at -78 - 20 ℃;

DOI:10.1021/jm1009742

Reference yield:

(R)-(1-chloro-2-phenylethyl)boronic acid (1R,2R,3S,5R)-(-)-2,3-pinanediol ester (88824-37-7) → (S)-(1-amino-2-phenylethyl)boronic acid (1R,2R,3S,5R)-(-)-2,3-pinanediol ester hydrochloride salt (178455-03-3)

Guidance literature:

(R)-(1-chloro-2-phenylethyl)boronic acid (1R,2R,3S,5R)-(-)-2,3-pinanediol ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

With hydrogenchloride; In 1,4-dioxane; diethyl ether; at -60 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.9b00735

upstream raw materials:

(+)-pinanediol (1R)-1-(N,N-bis(trimethylsilyl)amino)-2-phenylethaneboronate

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

benzyl bromide

pinacol benzylboronate

Refernces

• 1、 -. "Boronic acid derivatives". Paragraph 0098; 0121-0124; 0203; 0226-0229. . Retrieved 2021/07/21.
• 2、 Wang, Yao-Ling,Liu, Sha,Yu, Zhu-Jun,Lei, Yuan,Huang, Meng-Yi,Yan, Yu-Hang,Ma, Qiang,Zheng, Yang,Deng, Hui,Sun, Ying,Wu, Chengyong,Yu, Yamei,Chen, Qiang,Wang, Zhenling,Wu, Yong,Li, Guo-Bo. "Structure-based development of (1-(3′-Mercaptopropanamido)methyl)boronic Acid Derived Broad-Spectrum, Dual-Action Inhibitors of Metallo- And Serine-β-lactamases". . p. 7160 - 7184. Retrieved 2019/08/28.