147226-04-8

Basic information

• Product Name: N-CBZ-4-OXO-D-PROLINE
• Synonyms: N-CBZ-4-OXO-D-PROLINE;N-Cbz-4-oxo-D-proline Methyl ester;(R)-1-((Benzyloxy)carbonyl)-4-oxopyrrolidine-2-carboxylic acid
• CAS NO: 147226-04-8
• Molecular Formula: C₁₃H₁₃NO₅
• Molecular Weight: 263.25
• Mol File: 147226-04-8.mol

Chemical Properties

• Boiling Point: 488.5±45.0 °C(Predicted)
• Appearance: /
• Density: 1.408±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.83±0.20(Predicted)
• CAS DataBase Reference: N-CBZ-4-OXO-D-PROLINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-CBZ-4-OXO-D-PROLINE(147226-04-8)
• EPA Substance Registry System: N-CBZ-4-OXO-D-PROLINE(147226-04-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 147226-04-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-CBZ-4-OXO-D-PROLINE is used as a synthetic intermediate for the development of pharmaceuticals, leveraging its ability to facilitate the synthesis of complex organic molecules that are integral to the creation of new drugs and therapeutic agents.
Used in Peptide Synthesis:
In the field of peptide synthesis, N-CBZ-4-OXO-D-PROLINE is utilized as a key component, enabling the construction of peptide sequences that are vital for the development of bioactive peptides with potential applications in medicine and biotechnology.
Used in Organic Chemistry Research:
N-CBZ-4-OXO-D-PROLINE is employed as a research tool in organic chemistry, where it aids in the exploration of new synthetic pathways and the discovery of novel chemical reactions that can be applied to the synthesis of a wide range of organic compounds.

Upstream product

• 130930-25-5 (R,R)-4-hydroxy-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid 
• 51-35-4 4R-4-hydroxyproline 
• 501-53-1 benzyl chloroformate 
• 2584-71-6 cis-hydroxy-D-proline 

Downstream Products

• 870097-43-1 (R)-4-oxo-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 
• 870097-46-4 (5R,8R)-2,4-Dioxo-1,3,7-triaza-spiro[4.4]nonane-1,3,7,8-tetracarboxylic acid 7-benzyl ester 1,3,8-tri-tert-butyl ester 
• 870097-47-5 (3R,5R)-3-amino-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid 
• 900149-04-4 (3S,5R)-3-amino-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid 
• 870097-44-2 (5R,8R)-2,4-dioxo-1,3,7-triaza-spiro[4.4]nonane-7,8-dicarboxylic acid 7-benzyl ester 8-tert-butyl ester 
• 870097-45-3 (5S,8R)-2,4-dioxo-1,3,7-triaza-spiro[4.4]nonane-7,8-dicarboxylic acid 7-benzyl ester 8-tert-butyl ester 

Relevant articles and documents

An improved, scalable synthesis of bis-amino acids

trans-4-Hydroxy-L-proline derived bis-amino acids are chiral, cyclic building blocks that display two alpha-amino acids that are differentiated from each other with protecting groups. They are assembled into spiroligomers—rigid, shape-programmable spirocyclic oligomers that are both stereochemically and functionally diverse. The synthesis presented here focuses on recent improvements that allow for a convenient, large-scale synthesis of twelve stereochemically pure bis-amino acids from inexpensive trans-4-hydroxy-L-proline. The bis-amino acids differ in stereochemistry as well as the amine protecting group, one of which (para-nitrobenzyl carbamate) has not been previously incorporated into bis-amino acids.

The synthesis of curved and linear structures from a minimal set of monomers

Spiro-ladder oligomers of designed shape were assembled from a set of two enantiomeric bis-amino acid monomers. Two tetramers of differing monomer sequence were synthesized to study the effect of monomer stereochemistry upon macromolecular shape. Two-dime