23632-66-8

Basic information

• Product Name: (S)-(+)-3-(BENZYLOXYCARBONYL)-5-OXO-4-OXAZOLIDINEACETIC ACID
• Synonyms: (S)-(+)-3-(Benzyloxyxarbonyl)-5-ox-4-oxazolidineacetic Acid;(S)-(+)-3-(BENZYLOXYCARBONYL)-5-OXO-4-OXAZOLIDINEACETIC ACID;(S)-(+)-3-(benzyloxycarbonyl)-5-oxo-4-oxazolidine;(S)-2-(3-((Benzyloxy)carbonyl)-5-oxooxazolidin-4-yl)acetic acid
• CAS NO: 23632-66-8
• Molecular Formula: C₁₃H₁₃NO₆
• Molecular Weight: 279.25
• Product Categories: Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives
• Mol File: 23632-66-8.mol
• Article Data: 15

Chemical Properties

• Melting Point: 84-87 °C(lit.)
• Boiling Point: 555.6°Cat760mmHg
• Flash Point: 289.8°C
• Appearance: /
• Density: 1.411g/cm³
• Vapor Pressure: 3.53E-13mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 4.17±0.10(Predicted)
• CAS DataBase Reference: (S)-(+)-3-(BENZYLOXYCARBONYL)-5-OXO-4-OXAZOLIDINEACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-3-(BENZYLOXYCARBONYL)-5-OXO-4-OXAZOLIDINEACETIC ACID(23632-66-8)
• EPA Substance Registry System: (S)-(+)-3-(BENZYLOXYCARBONYL)-5-OXO-4-OXAZOLIDINEACETIC ACID(23632-66-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 23632-66-8(Hazardous Substances Data)

Usage

Uses

(S)-(+)-3-(Benzyloxyxarbonyl)-5-ox-4-oxazolidineacetic Acid is used in the preparation of Tryprostatin A and B. Also used in the synthesis of cyclic lactam analogs of α-melanotropin.

InChI:InChI=1/C13H13NO6/c15-11(16)6-10-12(17)20-8-14(10)13(18)19-7-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,15,16)/t10-/m0/s1

Upstream product

• 1152-61-0 N-Cbz-L-Asp 
• 50-00-0 formaldehyd 
• 67809-70-5 N-benzyloxycarbonyl-L-aspartic acid 

Downstream Products

• 126046-25-1 (S)-3-Benzyloxycarbonyl-4-<(N-tert-butoxycarbonyl)aminomethyl>-5-oxazolidinone 
• 172096-93-4 (4S)-N-Benzyloxycarbonyl₄-methoxycarbonylmethyl-1,3-oxazolidin-5-one 
• 23632-69-1 (S)-3-benzyloxycarbonyl-5-oxo-4-oxazolidine acetic acid tert-butyl ester 
• 1190604-51-3 C₁₃H₁₄N₂O₆ 
• 35909-93-4 dimethyl (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate 
• 1428260-93-8 C₁₄H₁₇NO₇ 
• 4668-42-2 (S)-2-benzyloxycarbonylamino-succinic acid 1-methyl ester 
• 153413-52-6 (S)-2-benzyloxycarbonylamino-3-chlorocarbonyl-propionic acid methyl ester 
• 1428260-94-9 (S)-diethyl (N-(benzyloxycarbonyl)-2-(3-oxo-4-(5-oxooxazolidin-4-yl))butyl)malonate 
• 1428261-05-5 (S)-diethyl (N-(benzyloxycarbonyl)-2-(3-oxo-4-(5-oxooxazolidin-4-yl))butyl)malonate 
• 1428261-04-4 (S)-N-Benzyloxycarbonyl-4-(2-oxobut-3-en-1-yl)oxazolidin-5-one 
• 1428260-91-6 C₂₂H₂₈N₂O₉ 
• 1428260-92-7 C₂₁H₂₈N₂O₉ 
• 1428261-10-2 C₂₁H₂₉N₃O₉ 

Relevant articles and documents

A Facile Synthesis of Hydroxamic Acids of Nα-Protected Amino Acids Employing BDMS, a Study of Their Molecular Docking and Their Antibacterial Activities

-

Antifungal dipeptides incorporating an inhibitor of homoserine dehydrogenase

The antifungal activity of 5-hydroxy-4-oxo-l-norvaline (HONV), exhibited under conditions mimicking human serum, may be improved upon incorporation of this amino acid into a dipeptide structure. Several HONV-containing dipeptides inhibited growth of human pathogenic yeasts of the Candida genus in the RPMI-1640 medium, with minimal inhibitory concentration values in the 32 to 64?μg?mL?1 range. This activity was not affected by multidrug resistance that is caused by overexpression of genes encoding drug efflux proteins. The mechanism of antifungal action of HONV dipeptides involved uptake by the oligopeptide transport system, subsequent intracellular cleavage by cytosolic peptidases, and inhibition of homoserine dehydrogenase by the released HONV. The relative transport rates determined the anticandidal activity of HONV dipeptides.

A microwave-assisted synthesis of (S)-N-protected homoserine γ-lactones from l-aspartic acid

A three-pot preparation of (S)-N-protected homoserine γ-lactones is presented. Conversion of N-protected l-aspartic acid to an oxazolidinone is followed by selective reduction/acid-catalyzed cyclization to deliver the lactones. Microwave irradiation proved valuable for improving the latter reaction steps in some cases.