97534-84-4

Basic information

• Product Name: (R)-(+)-3-(BENZYLOXYCARBONYL)-4-OXAZOLIDINECARBOXYLIC ACID
• Synonyms: (R)-CBZ-OXAPROLINE;(R)-Z-OXAPROLINE;(R)-(+)-3-Z-4-OXAZOLIDINECARBOXYLIC ACID;(R)-(+)-3-(BENZYLOXYCARBONYL)-4-OXAZOLIDINECARBOXYLIC ACID;(R)-(+)-3-CBZ-4-OXAZOLIDINECARBOXYLIC ACID;(R)-(+)-3-(Benzyloxycarbonyl)oxazolidine-4-carboxylic acid, 98%;(R)-(+)-3-(Benzyloxycarbonyl)-4-oxazolidinecarboxylic acid,98%;(R)-(+)-3-(Benzyloxycarbonyl)-4-oxazolidinecarboxylic acid(R)-CBZ-Oxaproline
• CAS NO: 97534-84-4
• Molecular Formula: C12H13NO5
• Molecular Weight: 251.24
• Product Categories: Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives
• Mol File: 97534-84-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 70-74 °C(lit.)
• Boiling Point: 454.8°C at 760 mmHg
• Flash Point: 228.9°C
• Appearance: /
• Density: 1.385
• Vapor Pressure: 4.61E-09mmHg at 25°C
• Refractive Index: 1.582
• PKA: 3.51±0.20(Predicted)
• CAS DataBase Reference: (R)-(+)-3-(BENZYLOXYCARBONYL)-4-OXAZOLIDINECARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-3-(BENZYLOXYCARBONYL)-4-OXAZOLIDINECARBOXYLIC ACID(97534-84-4)
• EPA Substance Registry System: (R)-(+)-3-(BENZYLOXYCARBONYL)-4-OXAZOLIDINECARBOXYLIC ACID(97534-84-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 97534-84-4(Hazardous Substances Data)

Usage

Description

(R)-(+)-3-(BENZYLOXYCARBONYL)-4-OXAZOLIDINECARBOXYLIC ACID is a chiral synthon derived from serine, characterized by its white powder form. It is a valuable intermediate in the field of organic chemistry, particularly for the asymmetric synthesis of various nitrogen-containing compounds.

Uses

Used in Pharmaceutical Industry:
(R)-(+)-3-(BENZYLOXYCARBONYL)-4-OXAZOLIDINECARBOXYLIC ACID is used as a chiral building block for the asymmetric synthesis of a wide range of nitrogen-containing pharmaceutical compounds. Its unique stereochemistry allows for the creation of enantiomerically pure products, which is crucial for the development of effective and safe drugs.
Used in Organic Synthesis:
In the field of organic synthesis, (R)-(+)-3-(BENZYLOXYCARBONYL)-4-OXAZOLIDINECARBOXYLIC ACID serves as a versatile chiral synthon, enabling the synthesis of complex nitrogen-containing molecules with high selectivity and yield. This makes it an essential component in the development of novel chemical entities and advanced materials.
Used in Research and Development:
(R)-(+)-3-(BENZYLOXYCARBONYL)-4-OXAZOLIDINECARBOXYLIC ACID is also utilized in research and development settings, where it aids chemists in exploring new synthetic routes and methodologies. Its unique properties and reactivity make it a valuable tool for studying the mechanisms of asymmetric reactions and the development of innovative catalytic systems.

InChI:InChI=1/C12H13NO5/c14-11(15)10-7-17-8-13(10)12(16)18-6-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,14,15)/t10-/m1/s1

Upstream product

• 50-00-0 formaldehyd 
• 1145-80-8 N-(benzyloxycarbonyl)-L-serine 
• 312-84-5 D-Serine 
• 501-53-1 benzyl chloroformate 
• 45521-08-2 (S)-oxazolidine-4-carboxylic acid 

Downstream Products

• 102081-70-9 4-benzylcarbamoyl-oxazolidine-3-carboxylic acid benzyl ester 

Relevant articles and documents

Asymmetric Total Synthesis of (+)-Neooxazolomycin Using a Chirality-Transfer Strategy

The total synthesis of (+)-neooxazolomycin was achieved from the amino-acid d-serine. The efficiency of this approach is derived from the use of principles of memory of chirality and dynamic kinetic resolution in the intramolecular aldol reaction of a serine derivative to build the densely functionalized lactam framework and to install three contiguous stereocenters. The key intermediate was readily elaborated to the target natural product.

The facile production of N-methyl amino acids via oxazolidinones

A range of oxazolidinones derived from N-carbamoyl α-amino acids were prepared by an efficient method as key intermediates in the synthesis of N-methyl amino acids and peptides. The method was readily applied to most α-amino acids except those with basic side chains. The oxazolidinones were converted by reductive cleavage into N-methyl α-amino acids. CSIRO 2000.

(Phosphinyloxy)acid amino acid inhibitors of angiotensin converting enzyme. 2. Terminal amino acid analogues of (S)-1-[6-Amino-2-[[hydroxy(4-phenylbutyl)phosphinyl]oxy]-1-oxohexyl]- L-proline

Analogues of (S)-1-[6-amino-2-[[hydroxy(4-phenylbutyl)phosphinyl]oxy]-1-oxohexyl]- L-proline (1, SQ 29,852) in which the terminal proline residue has been replaced by a variety of substituted and heteroatom-substituted prolines, N-arylglycines, N-cycloalkylglycines, and bicyclic amino acids have been synthesized and evaluated as inhibitors of angiotensin converting enzyme in vitro an in vivo. In general, the addition of lipophilic substituents to the 4-position of proline of the parent phosphate 1 resulted in substantial increases in vitro activity. The largest improvements were observed in the case of cis-benzyl (36-fold) and dithioketal (24-fold) analogues 2r and 2x, respectively. These enhancements of in vitro activity were accompanied by modest increases (2-3.5-fold) in in vivo (iv) activity. Among the various terminal amino acid replacements examined in this study, the indoline-based analogue 2i was by far the most potent compound on iv administration in the normotensive rat.