514820-49-6

Basic information

• Product Name: (R)-BoroPhe-(+)-Pinanediol-CF3CO2H
• Synonyms: (R)-BoroPhe-(+)-Pinanediol-CF3CO2H;(R)-Boro(5-Bromo)Bug-(+)-Pinanediol-HCl;(3aS,4S,6S,7aR)-Hexahydro-3a,5,5-trimethyl-alpha-(phenylmethyl)-4,6-methano-1,3,2-benzodioxaborole-2-methanamine trifluoroacetate
• CAS NO: 514820-49-6
• Molecular Formula: C₂HF₃O₂*C₁₈H₂₆BNO₂
• Molecular Weight: 413.24
• Mol File: 514820-49-6.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-BoroPhe-(+)-Pinanediol-CF3CO2H(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-BoroPhe-(+)-Pinanediol-CF3CO2H(514820-49-6)
• EPA Substance Registry System: (R)-BoroPhe-(+)-Pinanediol-CF3CO2H(514820-49-6)

Safety Data

• Hazardous Substances Data: 514820-49-6(Hazardous Substances Data)

Usage

General Description

(R)-BoroPhe-(+)-Pinanediol-CF3CO2H is a chiral organocatalyst used in asymmetric synthesis. It consists of a boron-containing compound and a chiral pinanediol ligand, with a trifluoroacetic acid group attached. This organocatalyst is used in a variety of reactions, including the synthesis of chiral compounds and pharmaceutical intermediates. It plays a crucial role in the formation of carbon-carbon and carbon-heteroatom bonds with high enantioselectivity, making it a valuable tool in organic chemistry. Its unique structure and reactivity make it an important component in the development of efficient and environmentally friendly synthetic methods.

Upstream product

• 78902-03-1 1-(S)-chloro-2-phenylethylboronic acid (1S,2S,3R,5S)-(+)-pinane-2,3-glycol ester 
• 76-05-1 trifluoroacetic acid 
• 18680-27-8 pinanediol 
• 4463-42-7 benzyl boronic acid 
• 78922-83-5 (1-phenylmethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester 

Downstream Products

• 1158974-99-2 (1R)-1-(N-tert-butoxycarbonyl-L-O-methyltyrosyl-L-valyl)amino-2-phenylethylboronic acid (+)-pinanediol ester 
• 1158974-92-5 C₈H₁₂BNO₂*ClH 
• 1440790-32-8 C₆₆H₉₁BN₆O₁₀ 
• 1440790-38-4 C₆₉H₉₆BN₇O₁₁ 
• 1440789-68-3 C₇₅H₁₀₀BN₇O₁₁ 

Relevant articles and documents

Structural optimization, biological evaluation, and application of peptidomimetic prostate specific antigen inhibitors

Prostate-specific antigen (PSA) is a serine protease produced at high levels by normal and malignant prostate epithelial cells that is used extensively as a biomarker in the clinical management of prostate cancer. To better understand PSA's role in prostate cancer progression, we prepared a library of peptidyl boronic acid-based inhibitors. To enhance selectivity for PSA vs other serine proteases, we modified the P1 site of the inhibitors to incorporate a bromopropylglycine group. This allowed the inhibitors to participate in halogen bond formation with the serine found at the bottom of the specificity pocket. The best of these Ahx-FSQn(boro)Bpg had PSA Ki of 72 nM and chymotrypsin Ki of 580 nM. In vivo studies using PSA-producing xenografts demonstrated that candidate inhibitors had minimal effect on growth but significantly altered serum levels of PSA. Biodistribution of 125I labeled peptides showed low levels of uptake into tumors compared to other normal tissues.