(S)-BoroVal-(-)-Pinanediol-hydrochloride

Base Information

• Chemical Name: (S)-BoroVal-(-)-Pinanediol-hydrochloride
• CAS No.: 1173167-11-7
• Molecular Formula: C₁₅H₂₈BNO₂*ClH
• Molecular Weight: 301.665
• Mol file: 1173167-11-7.mol

Synonyms:(S)-(1-amino-3-methylbutyl)boronic acid (1R,2R,3S,5R)-(-)-2,3-pinanediol ester hydrochloride salt

Chemical Property of (S)-BoroVal-(-)-Pinanediol-hydrochloride

Chemical Property:

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-BoroVal-(-)-Pinanediol-hydrochloride

There total 6 articles about (S)-BoroVal-(-)-Pinanediol-hydrochloride 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: 85.0%

2-methyl-4-chloro-butylboronic acid-(-)-α-pinanediol ester (1173167-09-3) → (S)-(1-amino-3-methylbutyl)boronic acid (1R,2R,3S,5R)-(-)-2,3-pinanediol ester hydrochloride salt (1173167-11-7,779357-85-6)

Guidance literature:

2-methyl-4-chloro-butylboronic acid-(-)-α-pinanediol ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20 ℃; for 18h; Inert atmosphere;

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

Reference yield:

C21H44BNO2Si2 → (S)-(1-amino-3-methylbutyl)boronic acid (1R,2R,3S,5R)-(-)-2,3-pinanediol ester hydrochloride salt (1173167-11-7,779357-85-6)

Guidance literature:

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

DOI:10.1021/jm9005093

Reference yield:

(1R,2R,3S,5R)-2,3-pinane diol (22422-34-0) → (S)-(1-amino-3-methylbutyl)boronic acid (1R,2R,3S,5R)-(-)-2,3-pinanediol ester hydrochloride salt (1173167-11-7,779357-85-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 23 h / 20 °C

2.1: zinc(II) chloride / diethyl ether / 22 h / -78 - 20 °C / Inert atmosphere

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 18 h / -78 - 20 °C / Inert atmosphere

3.2: -78 °C

With zinc(II) chloride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether;

upstream raw materials:

(-)-α-pinene

(1R,2R,3S,5R)-2,3-pinane diol

2-methyl-4-chloro-butylboronic acid-(-)-α-pinanediol ester

Downstream raw materials:

N-[(1S)-1-[[[(1S)-1-[(3aR,4R,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-2-phenyl]-1-(S)-(-)-1,2,3,4-tetrahydro-naphthoiccarboxamide

Refernces

• 1、 -. "Mercapto-amide boronic acid derivative and application thereof as MBL (metal beta-lactamase) and/or SBL (serine beta-lactamase) inhibitor". Paragraph 0114; 0115; 0120-0122; 0138-0140. . Retrieved 2019/09/14.
• 2、 Zhu, Yongqiang,Zhao, Xin,Zhu, Xinrong,Wu, Gang,Li, Yuejie,Ma, Yuheng,Yuan, Yunxia,Yang, Jie,Hu, Yang,Ai, Li,Gao, Qingzhi. "Design, synthesis, biological evaluation, and Structure-Activity Relationship (SAR) discussion of dipeptidyl boronate proteasome inhibitors, Part I: Comprehensive understanding of the SAR of α-amino acid boronates". supporting information; experimental part. p. 4192 - 4199. Retrieved 2010/01/16.