185121-37-3

Usage

Chemical structure

A complex chemical compound with multiple functional groups, including a pyrrolidinedicarboxylic acid core, a 1-(1,1-dimethylethyl) 2-methyl ester side chain, and a 3-[(1,1-dimethylethoxy)carbonyl]amino]-4-methoxy-4-oxobutyl functional group.

Stereochemistry

The (2S)configuration indicates that the compound has a specific stereochemistry, which is important for its biological activity and interactions with other molecules.

Functional groups

The compound contains several functional groups, including an amide, an ester, a carboxylic acid, and an ether, which contribute to its reactivity and potential applications.

Potential applications

Due to its intricate structure and diverse functional groups, 1,2-Pyrrolidinedicarboxylic acid, 5-[(3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-methoxy-4-oxobutyl]-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S)has potential applications in pharmaceuticals, organic synthesis, and biochemical research.

Solubility

The compound's solubility properties are not explicitly mentioned in the material provided, but its functional groups suggest that it may be soluble in polar solvents such as water, alcohols, or dimethyl sulfoxide (DMSO).

Stability

The stability of the compound is not explicitly mentioned in the material provided, but its functional groups suggest that it may be sensitive to hydrolysis, particularly the ester and amide groups.

Reactivity

The compound's reactivity is not explicitly mentioned in the material provided, but its functional groups suggest that it may undergo reactions such as hydrolysis, aminolysis, and esterification.

Structural complexity

The compound's structure is highly complex, with multiple chiral centers and functional groups, which may contribute to its potential applications in research and drug development.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 346441-81-4 (2S,7S)-5-(1,3-dioxolane)-2,8-bis[N-benzyloxycarbonylamino]nonane-1,9-dioic acid dimethyl ester 

Relevant academic research and scientific papers

An efficient approach to asymmetric synthesis of dipeptide β-turn mimetics: Indolizidinone amino acids

Azabicyclo[X.Y.0] alkane amino acids are rigid dipeptide β-turn mimetics with great potential applications for drug discovery. The lack of efficient methods to synthesize these compounds is a major bottleneck in this field. Herein we report an efficient a

Rigid dipeptide mimetics: Efficient synthesis of enantiopure indolizidinone amino acids

An effective means to synthesize indolizidinone amino acids has been developed and furnishes all possible stereoisomers of these conformationally rigid mimetics of peptide secondary structures. Inexpensive glutamic acid was employed as chiral educt in a Claisen condensation/reductive amination/lactam cyclization sequence that furnished stereoselectively azabicyclo[3.4.0]alkane amino acid 1. Enantiopure (3S,6S,9S)- and (3R,6R,9R)-2-oxo-3-N-(BOC)amino-1-azabicyclo[4.3.0]nonane-9-carboxylic acids ((3S,6S,9S)- and (3R,6R,9R)-1) were respectively synthesized from L- and D-N-(PhF)glutamates 2 (PhF = 9-(9-phenylfluorenyl)). Slow addition of sodium bis(trimethylsilyl)amide to 2 provided good to excellent yields of β-keto esters 3, which were subsequently hydrolyzed and decarboxylated to give symmetric α,ω-bis[N-(PhF)amino]azelate δ-ketones 5. Augmentation of hydrogen pressure increased diastereoselectivity in reductive aminations with 5 and afforded 5-alkylprolines 8 and 10. Lactam formation on exposure of 10 to triethylamine and N-protection with di-tert-butyl dicarbonate gave methyl-2-oxo-3-[N-(BOC)amino]-1-azabicyclo[4.3.0]nonane-9-carboxylate (12) which on C-terminal ester hydrolysis with hydroxide ion gave enantiopure [N-(BOC)amino]indolizidinone acid 1. Alternatively, hydride addition to ketone 5a gave symmetric α,ω-bis[N-(PhF)amino]azelate δ-alcohol 7a, which upon mesylation and intramolecular S(N)2 displacement by the PhF amine gave specifically cis-5-alkylproline 15 that was similarly converted to (3S,6S,9S)-1. In addition, epimerization of the C-9 stereocenter of (3S,6S,9S)-[N-(BOC)amino]indolizidinone methyl ester 12 with NaN(SiMe3)2 and ester hydrolysis gave (3S,6S,9R)-indolizidinone amino acid (3S,6S,9R)-1. By providing efficient methodology for synthesizing all of the possible stereoisomers of enantiopure indolizidinone amino acid 1, our route is specifically designed to enhance the general use of these peptide mimetics in the exploration of conformation-activity relationships of various biologically active peptides.