97534-82-2

Basic information

• Product Name: (S)-(-)-3-Z-4-OXAZOLIDINECARBOXYLIC ACID
• Synonyms: (S)-Z-OXAPROLINE;(S)-CBZ-OXAPROLINE;(S)-(-)-3-Z-4-OXAZOLIDINECARBOXYLIC ACID;(S)-(+)-3-CBZ-4-OXAZOLIDINECARBOXYLIC ACID;(S)-(-)-3-(BENZYLOXYCARBONYL)-4-OXAZOLIDINECARBOXYLIC ACID;(S)-(-)-3-(Benzyloxycarbonyl)oxazolidine-4-carboxylic acid, 98%;(S)-(-)-3-(benzyloxycarbonyl)-4-oxazolid-inecarbo;3,4-Oxazolidinedicarboxylic acid 3-(phenylmethyl) ester
• CAS NO: 97534-82-2
• Molecular Formula: C₁₂H₁₃NO₅
• Molecular Weight: 251.24
• Product Categories: Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives
• Mol File: 97534-82-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 74-78 °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
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: (S)-(-)-3-Z-4-OXAZOLIDINECARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-3-Z-4-OXAZOLIDINECARBOXYLIC ACID(97534-82-2)
• EPA Substance Registry System: (S)-(-)-3-Z-4-OXAZOLIDINECARBOXYLIC ACID(97534-82-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 97534-82-2(Hazardous Substances Data)

Usage

Chemical Properties

White powder

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-/m0/s1

Upstream product

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

Downstream Products

• 1307877-46-8 (-)-(S)-benzyl 4-[(2,6-dimethylphenyl)carbamoyl]-1,3-oxazolidine-3-carboxylate 
• 126111-22-6 (S)-3-<(phenylmethoxy)carbonyl>-4-oxazolidinecarboxylic acid methyl ester 
• 258830-56-7 (R)-4-[1-((S)-1-Carboxy-2-phenyl-ethyl)-1H-pyrazol-3-yl]-oxazolidine-3-carboxylic acid benzyl ester 
• 258833-67-9 (S)-2-[5-((R)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-pyrazol-1-yl]-3-phenyl-propionic acid methyl ester 
• 258833-79-3 (S)-2-[3-((R)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-pyrazol-1-yl]-3-phenyl-propionic acid methyl ester 
• 258830-44-3 (R)-4-[2-((S)-1-Carboxy-2-phenyl-ethyl)-2H-pyrazol-3-yl]-oxazolidine-3-carboxylic acid benzyl ester 
• 258833-69-1 (S)-2-[5-((R)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-pyrazol-1-yl]-4-methyl-pentanoic acid methyl ester 
• 258833-81-7 (S)-2-[3-((R)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-pyrazol-1-yl]-4-methyl-pentanoic acid methyl ester 
• 258830-60-3 (R)-4-[1-((S)-1-Carboxy-3-methyl-butyl)-1H-pyrazol-3-yl]-oxazolidine-3-carboxylic acid benzyl ester 
• 258830-48-7 (R)-4-[2-((S)-1-Carboxy-3-methyl-butyl)-2H-pyrazol-3-yl]-oxazolidine-3-carboxylic acid benzyl ester 
• 258833-80-6 (S)-2-[3-((R)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-pyrazol-1-yl]-3-methyl-butyric acid methyl ester 
• 258833-68-0 (S)-2-[5-((R)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-pyrazol-1-yl]-3-methyl-butyric acid methyl ester 
• 258830-58-9 (R)-4-[1-((S)-1-Carboxy-2-methyl-propyl)-1H-pyrazol-3-yl]-oxazolidine-3-carboxylic acid benzyl ester 

Relevant articles and documents

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.

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.