865704-45-6

Basic information

• Product Name: 4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutanoic acid
• Synonyms: 4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutanoic acid
• CAS NO: 865704-45-6
• Molecular Weight: 277.277
• Mol File: 865704-45-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutanoic acid(865704-45-6)
• EPA Substance Registry System: 4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutanoic acid(865704-45-6)

Safety Data

• Hazardous Substances Data: 865704-45-6(Hazardous Substances Data)

Upstream product

• 108-30-5 succinic acid anhydride 
• 40217-17-2 (R)-4-(phenylmethyl)-2-oxazolidinone 

Downstream Products

• 1424401-73-9 4-((R)-4-benzyl-2-oxooxazolidine-3-yl)-4-butyric acid allyl ester 
• 1424401-66-0 (S)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)pentanedioic acid allyl ester 
• 1424401-65-9 (S)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)pentanedioic acid 1-allyl ester 5-tert-butyl ester 
• 1424401-69-3 (S)-4-((R)-4-benzyl-2-oxazolidine-3-yl)-3-(tert-butoxycarbonylaminomethyl)-4-butanoic acid allyl ester 
• 1424401-67-1 (R)-3-((R)-4-benzyl-2-oxazolidine-3-carbonyl)pentanedioic acid allyl ester 
• 146093-85-8 (4R)-γ,2-dioxo-4-(phenylmethyl)-3-oxazolidinebutanoic acid methyl ester 
• 865704-56-9 tert-butyl (3S)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-({[(benzyloxy)carbonyl]amino}methyl)-4-oxobutanoate 
• 865704-55-8 benzyl (3R)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-{[(tert-butoxycarbonyl)amino]methyl}-4-oxobutanoate 
• 865704-48-9 1-benzyl 5-tert-butyl (3R)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}pentanedioate 
• 865704-59-2 (3S)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-({[(benzyloxy)carbonyl]amino}methyl)-4-oxobutanoic acid 
• 865704-51-4 (3S)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-5-(benzyloxy)-5-oxopentanoic acid 
• 865704-58-1 (3R)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-{[(tert-butoxycarbonyl)amino]methyl}-4-oxobutanoic acid 
• 865704-61-6 benzyl (3S)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-1-pyrrolidinecarboxylate 
• 865704-52-5 (3R)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-5-tert-butoxy-5-oxopentanoic acid 

Relevant articles and documents

Conjugates of modified cryptophycins and RGD-peptides enter target cells by endocytosis

Tumor targeting anticancer drug conjugates that contain a tumor recognition motif (homing device) are of high current relevance. Cryptophycins, naturally occurring cytotoxic cyclo-depsipeptides, have been modified by total synthesis to provide analogues suitable for conjugation to peptide-based homing devices. An array of functionalized β2-amino acids was synthesized and incorporated into cryptophycins. All analogues proved to be highly active in the cytotoxicity assay using the human cervix carcinoma cell line KB-3-1 and its multidrug-resistant subclone KB-V1. Conformational analysis of cryptophycin-52 and two synthetic analogues was performed by NMR and MD methods to obtain information on the influence of the unit C configuration on the overall conformation. An azide-functionalized cryptophycin was connected by CuAAC to an alkyne-containing fluorescently labeled cyclic RGD-peptide as the homing device for internalization studies. Confocal fluorescence microscopy proved integrin-mediated internalization by endocytosis and final lysosomal localization of the cryptophycin prodrug.

Chiral succinate: A precursor for enantiomerically pure β2-amino acids

Five suitably protected enantiomerically pure β2-amino acids, homologues of proteinogenic α-amino acids, were synthesized from the common chiral precursor, tert-butyl succinyloxazolidinone. Georg Thieme Verlag Stuttgart.