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

Description

(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 is a complex organic compound with a unique molecular structure. It is characterized by its hexahydro-3a,8,8-trimethyl-alpha-(2-methylpropyl)-4,6-methano-1,3,2-benzodioxaborole core, which is further functionalized with a 2-methanamine group and a 2,2,2-trifluoroacetate moiety. (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 is a white solid and is known for its potential applications in the pharmaceutical industry, particularly as an intermediate in the synthesis of Bortezomib (B675700), a boronic acid dipeptide derivative that acts as a proteasome inhibitor.

Uses

Used in Pharmaceutical Industry:
(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 is used as an intermediate in the synthesis of Bortezomib (B675700) for its role as a proteasome inhibitor. Proteasome inhibitors are important in the development of drugs targeting various diseases, including cancer, by disrupting the cellular protein degradation pathway and leading to the accumulation of misfolded proteins, ultimately causing cell death.
As a Bortezomib intermediate, this compound contributes to the development of therapeutic agents that can potentially treat multiple myeloma, mantle cell lymphoma, and other malignancies. Its unique structure and properties make it a valuable component in the design and synthesis of novel boronic acid dipeptide derivatives with improved pharmacological profiles and enhanced efficacy in combating cancer.

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

• 76-05-1 trifluoroacetic acid 
• 1173167-09-3 2-methyl-4-chloro-butylboronic acid-(-)-α-pinanediol ester 
• 22422-34-0 (1R,2R,3S,5R)-2,3-pinane diol 
• 1135491-84-7 (1S)-(S)-pinanediol 1-bis(trimethylsilyl)amino-3-methylbutane-1-boronate 
• 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 
• 85167-14-2 (3aS,4S,6S,7aR)-2-[(1S)-1-chloro-3-methylbutyl]-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborole 
• 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 
• 108-18-9 diisopropylamine 
• 4111-54-0 lithium diisopropyl amide 

Downstream Products

• 179324-69-7 velcade 
• 179324-79-9 ((R)-1-((S)-2-benzamido-3-phenylpropanamido)-3-methylbutyl)boronic Acid 
• 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 
• 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 
• 1187479-72-6 (1S,2S,3R,5S)-pinanediol N-BOC-L-phenylalanine-L-leucine boronate 

Relevant articles and documents

De Novo Design of Boron-Based Peptidomimetics as Potent Inhibitors of Human ClpP in the Presence of Human ClpX

Boronic acids have attracted the attention of synthetic and medicinal chemists due to boron's ability to modulate enzyme function. Recently, we demonstrated that boron-containing amphoteric building blocks facilitate the discovery of bioactive aminoboronic acids. Herein, we have augmented this capability with a de novo library design and a virtual screening platform modified for covalent ligands. This technique has allowed us to rapidly design and identify a series of α-aminoboronic acids as the first inhibitors of human ClpXP, which is responsible for the degradation of misfolded proteins.

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