487048-27-1

Basic information

• Product Name: (2S)-N-BOC-CIS-4-BROMO-L-PROLINE T-BUTYL ESTER
• Synonyms: (2S)-N-BOC-CIS-4-BROMO-L-PROLINE T-BUTYL ESTER
• CAS NO: 487048-27-1
• Molecular Formula: C₁₄H₂₄BrNO₄
• Molecular Weight: 350.25
• Product Categories: pharmacetical
• Mol File: 487048-27-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 373.6°Cat760mmHg
• Flash Point: 179.7°C
• Appearance: /
• Density: 1.304g/cm³
• Vapor Pressure: 8.87E-06mmHg at 25°C
• Refractive Index: 1.503
• CAS DataBase Reference: (2S)-N-BOC-CIS-4-BROMO-L-PROLINE T-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-N-BOC-CIS-4-BROMO-L-PROLINE T-BUTYL ESTER(487048-27-1)
• EPA Substance Registry System: (2S)-N-BOC-CIS-4-BROMO-L-PROLINE T-BUTYL ESTER(487048-27-1)

Safety Data

• Hazardous Substances Data: 487048-27-1(Hazardous Substances Data)

Usage

Description

(2S)-N-BOC-CIS-4-BROMO-L-PROLINE T-BUTYL ESTER is a chemical compound with the molecular formula C14H22BrNO4. It is an ester derivative of (2S)-N-BOC-CIS-4-BROMO-L-PROLINE, a proline derivative that is often used in the synthesis of peptides and other organic compounds. The t-butyl ester moiety in this compound provides stability and protection to the proline moiety, allowing for its use in various chemical reactions and processes.

Uses

Used in Pharmaceutical and Biotechnological Research:
(2S)-N-BOC-CIS-4-BROMO-L-PROLINE T-BUTYL ESTER is used as a building block for the development of new drugs and therapeutic agents. Its stability and protection provided by the t-butyl ester moiety make it suitable for use in various chemical reactions and processes in the synthesis of peptides and other organic compounds.

InChI:InChI=1/C14H24BrNO4/c1-13(2,3)19-11(17)10-7-9(15)8-16(10)12(18)20-14(4,5)6/h9-10H,7-8H2,1-6H3/t9-,10-/m0/s1

Upstream product

• 170850-75-6 BOC-Hyp-OtBu 
• 24424-99-5 di-tert-butyl dicarbonate 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 51-35-4 4R-4-hydroxyproline 

Downstream Products

• 90600-20-7 (2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid 

Relevant articles and documents

Locked conformations for proline pyrrolidine ring: Synthesis and conformational analysis of cis- and trans-4-tert-butylprolines

The motional restrictions of the proline pyrrolidine ring allow this secondary amine amino acid to act as a turn inducer in many peptides and proteins. The pyrrolidine ring is known to exhibit two predominant pucker modes (i.e., C-4 (Cγ) exo and endo envelope conformers whose ratio can be controlled by proper substituents in the ring). In nature, the exo puckered 4(R)-hydroxy-L-proline plays a crucial role as a building block in collagen and collagen-like structures. It has been previously concluded that the electronegativity of the 4-cis-substituent increases the endo puckering while the electronegativity of the 4-trans-substituent favors the exo puckering. Here, we have introduced a sterically demanding tert-butyl group at C-4 in trans- and cis-configurations. In the case of trans-substitution, the induced puckering effect on the pyrrolidine ring was studied with X-ray crystallography and 1H NMR spectral simulations. Both cis- and trans-4-tert-butyl groups strongly favor pseudoequatorial orientation, thereby causing opposite puckering effects for the pyrrolidine ring, cis-exo and trans-endo for L-prolines, in contrast to the effects observed in the case of electronegative C-4 substituents. The syntheses and structural analysis are presented for the conformationally constrained 4-tert-butylprolines. The prolines were synthesized from 4-hydroxy-L-proline, substitution with t-BuCuSPhLi being the key transformation. This reaction gave N-Boc-trans-4-tert-butyl-L-proline tert-butyl ester in 94% ee and 57% de. Enantioselectivity was increased to 99.2% ee by crystallization of N-Boc-trans-4-tert-butyl-L-proline in the final step of the synthesis.