132682-05-4

Basic information

• Product Name: tert-butyl (2-(((benzyloxy)carbonyl)amino)-2-methylpropanoyl)-L-prolinate
• Synonyms: tert-butyl (2-(((benzyloxy)carbonyl)amino)-2-methylpropanoyl)-L-prolinate
• CAS NO: 132682-05-4
• Molecular Weight: 390.48
• Mol File: 132682-05-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: tert-butyl (2-(((benzyloxy)carbonyl)amino)-2-methylpropanoyl)-L-prolinate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (2-(((benzyloxy)carbonyl)amino)-2-methylpropanoyl)-L-prolinate(132682-05-4)
• EPA Substance Registry System: tert-butyl (2-(((benzyloxy)carbonyl)amino)-2-methylpropanoyl)-L-prolinate(132682-05-4)

Safety Data

• Hazardous Substances Data: 132682-05-4(Hazardous Substances Data)

Upstream product

• 15030-72-5 Z-Aib-OH 
• 5497-76-7 L-proline tert-butyl ester hydrochloride 
• 367274-56-4 Z-Aib-F 
• 83283-35-6 Proline tert-butyl ester dibenzenesulfimide salt 
• 2812-46-6 proline tert-butyl ester 

Downstream Products

• 128422-13-9 Z-L-Leu-Aib-Pro-OtBu 
• 132682-09-8 H-Aib-Pro-OtBu*HCl 

Relevant articles and documents

Metal-free approach for hindered amide-bond formation with hypervalent iodine(iii) reagents: application to hindered peptide synthesis

A new bio-inspired approach is reported for amide and peptide synthesis using α-amino esters that possess a potential activating group (PAG) at the ester residue. To activate the ester functionality under mild metal-free conditions, we exploited the facile dearomatization of phenols with hypervalent iodine(iii) reagents. Using a pyridine-hydrogen fluoride complex, highly reactive acyl fluoride intermediates can be successfully generated, thereby allowing for the smooth formation of sterically hindered amides and peptides from bulky amines and α-amino esters, respectively.

PyBOP and PyBroP: Two reagents for the difficult coupling of the α,α-dialkyl amino acid, Aib

The difficult coupling of α-aminoisobutyric acid (Aib) was carried out using PyBOP and PyBroP in a comparative study with BOP and BroP. These reagents gave good results under simple conditions (one pot, r.t., 1h). Coded amino acids could be coupled with Aib using PyBOP under standard conditions of peptide synthesis without racemization whereas the coupling of two Aib residues required PyBroP/DMAP. A fragment containing an Aib C-terminal could be coupled without epimerization of the penultimate residue.