660852-86-8

Basic information

• Product Name: (R)-2,2-DIMETHYL-OXAZOLIDINE-3,4-DICARBOXYLIC ACID 3-TERT-BUTYL ESTER
• Synonyms: (R)-2,2-DIMETHYL-OXAZOLIDINE-3,4-DICARBOXYLIC ACID 3-TERT-BUTYL ESTER;(R)-3-(TERT-BUTOXYCARBONYL)-2,2-DIMETHYLOXAZOLIDINE-4-CARBOXYLIC ACID
• CAS NO: 660852-86-8
• Molecular Formula: C₁₁H₁₉NO₅
• Molecular Weight: 245.27
• Product Categories: pharmacetical
• Mol File: 660852-86-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 358.2±42.0 °C(Predicted)
• Appearance: /
• Density: 1.175±0.06 g/cm3(Predicted)
• PKA: 3.55±0.40(Predicted)
• CAS DataBase Reference: (R)-2,2-DIMETHYL-OXAZOLIDINE-3,4-DICARBOXYLIC ACID 3-TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2,2-DIMETHYL-OXAZOLIDINE-3,4-DICARBOXYLIC ACID 3-TERT-BUTYL ESTER(660852-86-8)
• EPA Substance Registry System: (R)-2,2-DIMETHYL-OXAZOLIDINE-3,4-DICARBOXYLIC ACID 3-TERT-BUTYL ESTER(660852-86-8)

Safety Data

• Hazardous Substances Data: 660852-86-8(Hazardous Substances Data)

Usage

General Description

The chemical compound (R)-2,2-DIMETHYL-OXAZOLIDINE-3,4-DICARBOXYLIC ACID 3-TERT-BUTYL ESTER is a derivative of oxazolidine-3,4-dicarboxylic acid, containing a (R)-2,2-dimethyl oxazolidine group and a tert-butyl ester group. It is a chiral compound, meaning it has a non-superimposable mirror image (enantiomer), and the (R)- designation indicates its stereochemistry. (R)-2,2-DIMETHYL-OXAZOLIDINE-3,4-DICARBOXYLIC ACID 3-TERT-BUTYL ESTER may have potential applications in pharmaceutical and medicinal chemistry, as well as in organic synthesis. Its properties and uses may include its role as a chiral building block in the synthesis of other compounds, and also its potential biological activity or pharmacological effects. Research and development of this compound may focus on its potential applications in drug discovery, as well as its chemical and structural properties for use in organic chemistry reactions and as a chiral resolving agent.

Upstream product

• 136703-59-8 (3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester 
• 3262-72-4 (R)-N-tert-butoxycarbonyl serine 
• 77-76-9 2,2-dimethoxy-propane 
• 83345-44-2 3-tert-butoxycarbonylamino-4-hydroxy-butyric acid 
• 95715-85-8 2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 108149-60-6 methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate 

Downstream Products

• 896746-83-1 (R)-4-(2-benzoyl-phenylcarbamoyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 1822572-30-4 4-(methoxymethylcarbamoyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 
• 1242185-14-3 (R)-tert-butyl 4-(2-(4-bromobenzoyl)phenylcarbamoyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1242185-13-2 (R)-tert-butyl 4-(2-benzoyl-4-chlorophenylcarbamoyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 95715-87-0 (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine 
• 167102-62-7 (R)-N,O-isopropylidenyl-2-(N-tert-butyloxycarbonylamino)-3-oxo-propanamide-N,O-dimethyl-hydroxyamine 
• 1443753-94-3 C₁₈H₂₅NO₆ 
• 1443753-93-2 (3S,4S)-benzyl N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-methyl-5-oxopentanoate 
• 167102-63-8 (R)-N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-oxo-2-butanone 
• 1308272-25-4 C₃₉H₄₆BrF₂NO₉ 
• 1310683-93-2 C₁₉H₂₆N₂O₅ 

Relevant articles and documents

ISOINDOLINE COMPOSITIONS AND METHODS FOR TREATING NEURODEGENERATIVE DISEASE

Isoindoline sigma-2 receptor antagonist compounds, pharmaceutical compositions comprising such compounds, and methods for inhibiting Abeta- associated synapse loss or synaptic dysfunction in neuronal cells, modulating an Abeta-associated membrane trafficking change in neuronal cells, and treating cognitive decline associated with Abeta pathology are provided.

Synthesis of a novel series of 2,3,4-trisubstituted oxazolidines designed by isosteric replacement or rigidification of the structure and cytotoxic evaluation

We have previously reported on a study of the structure-activity relationship in a series of 2,3,4-substituted oxazolidines recently discovered by our group varying the substituent at the ring or stereochemistry of the oxazolidine ring. We discovered the cytotoxic and pro-apoptotic potential of compounds 1 and 2 with good selectivity against cancer cell lines. In the present study we describe the synthesis and cytotoxic evaluation against cancer cell lines (HL60, JURKAT, MDA-MB-231 and LNCaP) of a series of oxazolidines designed by isosteric replacement or rigidification of the oxymethylene spacer of compounds 1 and 2. Alkenes 3 and 4 retained the activity against MDA-MB-231 cells and they were more active on HL60, JURKAT and LNCaP cells. Considering LNCaP cells, E-isomer 4 was at least 7 times and about 3 times more potent than lead 1 and Z-isomer 3, respectively. Compound 4 exerted significant activity against LNCaP with IC50 in the low micromolar range (11 μM) without affecting VERO cells and PBMC proliferation (IC50 > 100 μM) indicating its low toxicity to normal cells.

Effects on polo-like kinase 1 polo-box domain binding affinities of peptides incurred by structural variation at the phosphoamino acid position

Protein-protein interactions (PPIs) mediated by the polo-box domain (PBD) of polo-like kinase 1 (Plk1) serve important roles in cell proliferation. Critical elements in the high affinity recognition of peptides and proteins by PBD are derived from pThr/pS