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

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

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.

Synthesis of N-protected N-methyl serine and threonine

Two efficient and convenient syntheses of N-Cbz and N-Fmoc N-methyl serine and threonine are described. The amino acid side-chain alcohol can be protected as a TBDMS ether in very good yield or left free, followed by the formation and subsequent reduction of the corresponding oxazolidinone.

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.

Optically Active 4-Oxaproline Derivatives: New Useful Chiral Synthons Derived from Serine and Threonine

A very simple procedure for the preparation of chiral optically active N-protected-4-carboxy-1,3-oxazolidine (4-oxaproline) derivatives starting from serine and threonine is described which avoids the use of toxic solvents or reagents.Elaboration of these compounds allows significant improvement in the handling of serine and threonine during the multigram preparation of oligopeptide structures and affords versatile chiral building blocks for the organic synthesis.

(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.