179324-87-9

Basic information

• Product Name: (aR,3aS,4S,6S,7aR)-Hexahydro-3a,8,8-trimethyl-alpha-(2-methylpropyl)-4,6-methano-1,3,2-benzodioxaborole-2-methanamine 2,2,2-trifluoroacetate
• Synonyms: (1R)-(S)-PINANEDIOL 1-AMMONIUM TRIFLUOROACETATE-3-METHYLBUTANE-1-BORONATE;(R)-BoroLeu-(+)-Pinanediol-CF3COOH;(R)-BoroLeu-(+)-Pinanediol-CF3CO2H;(aR,3aS,4S,6S,7aR)-Hexahydro-3a,8,8-trimethyl-alpha-(2-methylpropyl)-4,6-methano-1,3,2-benzodioxaborole-2-methanamine 2,2,2-trifluoroacetate;(αR)-(1S,2S,3R,5S)-Pinanediol-1-amino-3-methylbutane-1-boronate Trifluoroacetate;Bortezomib Intermediate 1;Pinanedioltrifluoroacetate salt-;(R)-BoroLeu-(+)-Pinanediol trifluoroacetate
• CAS NO: 179324-87-9
• Molecular Formula: C15H28BNO2.C2HF3O2
• Molecular Weight: 379.224
• EINECS: 2017-001-1
• Product Categories: Amines;Boron Derivatives;Chiral Reagents;Intermediates
• Mol File: 179324-87-9.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Ethanol (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (aR,3aS,4S,6S,7aR)-Hexahydro-3a,8,8-trimethyl-alpha-(2-methylpropyl)-4,6-methano-1,3,2-benzodioxaborole-2-methanamine 2,2,2-trifluoroacetate(CAS DataBase Reference)
• NIST Chemistry Reference: (aR,3aS,4S,6S,7aR)-Hexahydro-3a,8,8-trimethyl-alpha-(2-methylpropyl)-4,6-methano-1,3,2-benzodioxaborole-2-methanamine 2,2,2-trifluoroacetate(179324-87-9)
• EPA Substance Registry System: (aR,3aS,4S,6S,7aR)-Hexahydro-3a,8,8-trimethyl-alpha-(2-methylpropyl)-4,6-methano-1,3,2-benzodioxaborole-2-methanamine 2,2,2-trifluoroacetate(179324-87-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 179324-87-9(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 179324-87-9 differently. You can refer to the following data:
1. Bortezomib intermediate
2. Bortezomib (B675700) intermediate. A boronic acid dipeptide derivative as proteasome inhibitors.

InChI:InChI=1/C15H28BNO2.C2HF3O2/c1-9(2)6-13(17)16-18-12-8-10-7-11(14(10,3)4)15(12,5)19-16;3-2(4,5)1(6)7/h9-13H,6-8,17H2,1-5H3;(H,6,7)/t10-,11-,12+,13-,15-;/m0./s1

Upstream product

• 1135491-84-7 (1S)-(S)-pinanediol 1-bis(trimethylsilyl)amino-3-methylbutane-1-boronate 
• 76-05-1 trifluoroacetic acid 
• 514820-48-5 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 
• 1173167-09-3 2-methyl-4-chloro-butylboronic acid-(-)-α-pinanediol ester 
• 22422-34-0 (1R,2R,3S,5R)-2,3-pinane diol 
• 85167-14-2 (3aS,4S,6S,7aR)-2-[(1S)-1-chloro-3-methylbutyl]-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborole 
• 108-18-9 diisopropylamine 
• 4111-54-0 lithium diisopropyl amide 
• 179324-86-8 (1R)-3-methyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0^2,6]decan-4-yl]butan-1-amine 
• 87249-60-3 (3aS,4S,6S,7aR)-2-(dichloromethyl)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole 
• 18680-27-8 pinanediol 
• 84110-34-9 2-(2-methylpropyl)-(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole 

Downstream Products

• 179324-69-7 velcade 
• 179324-79-9 ((R)-1-((S)-2-benzamido-3-phenylpropanamido)-3-methylbutyl)boronic Acid 
• 1201903-02-7 2,5-dichloro-N-[2-({(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexa-hydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}amino)-2-oxoethyl]benzamide 
• 205393-22-2 N-[(1S)-1[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-2-benzyl]2-pyrazine carboxamide 
• 1187479-72-6 (1S,2S,3R,5S)-pinanediol N-BOC-L-phenylalanine-L-leucine boronate 

Relevant articles and documents

SUBSTITUTED BORIC ACID COMPOUND, PHARMACEUTICAL COMPOSITION COMPRISING SAME, AND APPLICATION THEREOF

A substituted boric acid compound, a pharmaceutical composition comprising same, and an application thereof. The substituted boric acid compound is a compound represented by formula (I), or a crystal form, a pharmaceutically acceptable salt, a prodrug, a stereoisomer, a hydrate, or a solvent compound thereof. The boric acid compound has proteasome inhibitory activity, good pharmacodynamic/pharmacokinetic performance, good applicability, and high safety, and can be used for preparing drugs for treating diseases related to proteasomes.

Preparation of (1R)-(S)-pinane diol-1-amino-3-methyl-butane-1-borate and a salt thereof

The invention discloses a method for preparing (1R)-(S)-pinanediol-1-amino-3-methylbutane-1-borate ester and a salt thereof. The method for preparing (1R)-(S)-pinanediol-1-amino-3-methylbutane-1-borate ester comprises step A and step B in the following synthetic route, wherein in the formula, X represents a halogen atom and M represents an alkali metal. (1R)-(S)-pinanediol-1-amino-3-methylbutane-1-borate ester is subjected to a salt forming reaction with an organic acid or an inorganic aid, and an acidic salt of (1R)-(S)-pinanediol-1-amino-3-methylbutane-1-borate ester is obtained. The method of the invention can help to synthesize high-purity bortezomib or other boropeptide compounds in low cost, is accord with industrial production requirements and has practical value.

Systematic comparison of peptidic proteasome inhibitors highlights the α-ketoamide electrophile as an auspicious reversible lead motif

The ubiquitin-proteasome system (UPS) has been successfully targeted by both academia and the pharmaceutical industry for oncological and immunological applications. Typical proteasome inhibitors are based on a peptidic backbone endowed with an electrophi