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

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

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 
• 85167-14-2 (3aS,4S,6S,7aR)-2-[(1S)-1-chloro-3-methylbutyl]-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborole 
• 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 
• 108-18-9 diisopropylamine 
• 4111-54-0 lithium diisopropyl amide 
• 1135491-84-7 (1S)-(S)-pinanediol 1-bis(trimethylsilyl)amino-3-methylbutane-1-boronate 
• 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 
• 1624284-01-0 (R)-1-{(S)-2-[2-oxo-4-(phenylamino)pyridin-1(2H)-yl]-3-phenylpropanamido}-3-methylbutylboronic acid pinanediol ester 
• 1624283-56-2 (S)-N-isopentyl-2-[2-oxo-4-(phenylamino)pyridin-1(2H)-yl]-3-phenylpropanamide 
• 1624284-00-9 (R)-1-{3-[2-oxo-3-(phenylamino)pyridin-1(2H)-yl]propanamido}-3-methylbutylboronic acid pinanediol ester 
• 1624283-54-0 N-isopentyl-3-[4-(4-Methoxyphenylamino)-2-oxo-2H-pyridin-1-yl]propionamide 
• 1624283-97-1 (R)-1-{3-[4-(4-methoxyphenylamino)-2-oxopyridin-1(2H)-yl]propanamido}-3-methylbutylboronic acid pinanediol ester 
• 1624283-96-0 (R)-1-{3-[4-(3-ethylphenylamino)-2-oxopyridin-1(2H)-yl]propanamido}-3-methylbutylboronic acid pinanediol ester 
• 1624283-53-9 N-isopentyl-3-(2-oxo-4-phenylamino-2H-pyridin-1-yl)propionamide 
• 1624283-95-9 (R)-1-{3-[2-oxo-4-(phenylamino)pyridin-1(2H)-yl]propanamido}-3-methylbutylboronic acid pinanediol ester 
• 1624283-92-6 (R)-1-{2-[2-oxo-3-(phenylamino)pyridin-1(2H)-yl]acetamido}-3-methylbutylboronic acid pinanediol ester 
• 1624283-50-6 N-isopentyl-2-(2-oxo-3-phenylamino-2H-pyridin-1-yl)acetamide 
• 1624283-91-5 (R)-1-{2-[4-(benzylamino)-2-oxopyridin-1(2H)-yl]acetamido}-3-methylbutylboronic acid pinanediol ester 
• 1624283-49-3 2-[4-(4-methoxyphenylamino)-2-oxo-2H-pyridin-1-yl]-N-isopentylacetamide 

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.

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.

NOVEL BORONIC ACID DERIVATIVES AS ANTI CANCER AGENTS

The invention relates to synthesis and anticancer activity of novel boronic acid derivatives of formula 5 or pharmaceutical acceptable salts and esters thereof. Anti cancer activity of the compounds is evaluated by in vitro study on cancer cell lines like

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

PROCESS FOR THE PREPARATION OF BORTEZOMIB

The present invention relates to a process for the preparation of bortezomib (Formula I) and its intermediates.

Design, synthesis and biological evaluation of novel analogs of bortezomib

Novel analogs of bortezomib were designed, synthesized and in vitro biological evaluation was carried out using human tumor cell lines A549 and PC3. Docking studies of these analogs of bortezomib was discussed. According to biological investigations, the inhibitors 4, 6, and 8 were found to be more potent than reference drug candidate bortezomib. A549 cell line showed significant sensitivity towards 4, 6, and 8 with IC50 values 14.03, 18.5, and 12.4 nM, respectively, and PC3 cell line showed IC50 values 26.1, 37.0, and 21.2 nM, respectively. The IC50 values of bortezomib in these cell lines are 27.3 nM and 42.0 nM. Copyright

PROCESS FOR THE PREPARATION OF BORTEZOMIB

The present invention relates to a process for the preparation of bortezomib (Formula I) and its intermediates.

A convergent approach to synthesis of bortezomib: the use of TBTU suppresses racemization in the fragment condensation

Bortezomib is a first-in-class therapeutic antineoplastic agent used for treating patients with multiple myeloma and mantle cell lymphoma. In this paper we report an improved method for synthesis of the title compound using a convergent approach. TBTU was

METHODS FOR PREPARING BORTEZOMIB AND INTERMEDIATES USED IN ITS MANUFACTURE

Provided herein are methods for preparing bortezomib and intermediates useful in the preparation of bortezomib. The present methods unexpectedly provide superior yields and purities, including optical purities, of bortezomib and the intermediates for the preparation of bortezomib.