(R)-BoroLeu-(+)-Pinanediol-HCl

Base Information

• Chemical Name: (R)-BoroLeu-(+)-Pinanediol-HCl
• CAS No.: 779357-85-6
• Molecular Formula: C₁₅H₂₈BNO₂*(x)ClH
• Molecular Weight: 301.663
• Mol file: 779357-85-6.mol

Synonyms:4,6-Methano-1,3,2-benzodioxaborole-2-methanamine,hexahydro-3a,5,5-trimethyl-a-(2-methylpropyl)-, hydrochloride, (aR,3aS,4S,6S,7aR)- (9CI);

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

Chemical Property:

• Appearance/Colour: off-white solid
• Melting Point: 176-178 °C
• PSA: 44.48000
• LogP: 4.54950
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Dimethylformamide, Ethanol, Methanol, Tetrahydrofuran,

Purity/Quality:

99% ^*data from raw suppliers

(αR)-(1S,2S,3R,5S)-Pinanediol-1-amino-3-methylbutane-1-boronateHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 29 articles about (R)-BoroLeu-(+)-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: 96.0%

1,1,1-trimethyl-N-{(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}-N-(trimethylsilyl)silanamine (514820-48-5) → (1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxabor-ol-2-yl]butan-1-amine hydrochloride (779357-85-6)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; diethyl ether; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/jo901930v

Reference yield: 95.0%

(3aS,4S,6S,7aR)-2-[(1S)-1-chloro-3-methylbutyl]-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborole (85167-14-2) → (1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxabor-ol-2-yl]butan-1-amine hydrochloride (779357-85-6)

Guidance literature:

(3aS,4S,6S,7aR)-2-[(1S)-1-chloro-3-methylbutyl]-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborole; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20 ℃;

With hydrogenchloride; In 1,4-dioxane; diethyl ether; water; at 0 - 20 ℃; for 4h; Inert atmosphere;

DOI:10.1021/acs.orglett.9b00584

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 ℃;

upstream raw materials:

1,1,1-trimethyl-N-{(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}-N-(trimethylsilyl)silanamine

2-[(1S)-1-chloro-3-methylbutyl]-(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole

(3aS,4S,6S,7aR)-2-[(1S)-1-chloro-3-methylbutyl]-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborole

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

Downstream raw materials:

N-[(1R)-3-methyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decan-4-yl]butyl]-1-{2-[(2,3,4-trimethoxyphenyl)formamido]ethyl}-1H-1,2,3-triazole-4-carboxamide

C₃₂H₄₉BN₂O₇

C₃₁H₄₇BN₂O₇

Refernces

• 1、 Hinkes, Stefan P.A.,Klein, Christian D.P.. "Virtues of Volatility: A Facile Transesterification Approach to Boronic Acids". supporting information. p. 3048 - 3052. Retrieved 2019/05/10.
• 2、 -. "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.