Methyl 1-Cbz-azetidine-3-carboxylate - CAS 757239-60-4

Methyl 1-Cbz-azetidine-3-carboxylate - CAS 757239-60-4 Catalog number: BADC-01931

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Methyl 1-Cbz-azetidine-3-carboxylate is a non-cleavable ADC linker and also an alkyl chain-based PROTAC linker.

Category
ADCs Linker
Product Name
Methyl 1-Cbz-azetidine-3-carboxylate
CAS
757239-60-4
Catalog Number
BADC-01931
Molecular Formula
C13H15NO4
Molecular Weight
249.26
Purity
97.0%
Methyl 1-Cbz-azetidine-3-carboxylate

Ordering Information

Catalog Number Size Price Quantity
BADC-01931 -- $-- Inquiry
Description
Methyl 1-Cbz-azetidine-3-carboxylate is a non-cleavable ADC linker and also an alkyl chain-based PROTAC linker.
Synonyms
Azetidine-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester; 1,3-Azetidinedicarboxylic acid, 3-methyl 1-(phenylmethyl) ester
IUPAC Name
1-O-benzyl 3-O-methyl azetidine-1,3-dicarboxylate
Canonical SMILES
COC(=O)C1CN(C1)C(=O)OCC2=CC=CC=C2
InChI
InChI=1S/C13H15NO4/c1-17-12(15)11-7-14(8-11)13(16)18-9-10-5-3-2-4-6-10/h2-6,11H,7-9H2,1H3
InChIKey
VMBHUIMZBSWWCN-UHFFFAOYSA-N
Density
1.3±0.1 g/cm3
Boiling Point
414.9±45.0 °C at 760 mmHg

Methyl 1-Cbz-azetidine-3-carboxylate is a valuable compound in organic synthesis and pharmaceutical research, with several key applications. Here are some of its primary applications:

Peptide Synthesis: Methyl 1-Cbz-azetidine-3-carboxylate is used as a building block in the synthesis of peptides, particularly those containing azetidine ring structures. Its stable carbamate protective group, Cbz, allows for selective deprotection under mild conditions, making it versatile in peptide chemistry. This aids researchers in developing novel peptides for therapeutic and research purposes.

Pharmaceutical Development: This compound serves as an intermediate in the synthesis of various pharmaceuticals, particularly those targeting special ring structures for improved drug efficacy. Its unique reactive properties facilitate the construction of complex molecular architectures in drug discovery. Researchers leverage this versatility to optimize drug candidates, enhancing bioavailability and stability.

Chiral Synthesis: Methyl 1-Cbz-azetidine-3-carboxylate is used in asymmetric synthesis to introduce chirality in pharmaceutical compounds and other active molecules. It acts as a key chiral auxiliary or precursor that enables the synthesis of enantiomerically pure products. This is crucial for the development of drugs where stereochemistry significantly impacts therapeutic outcomes.

Chemical Research: Researchers utilize this compound in studying reaction mechanisms and exploring new synthetic methodologies. Its structure allows chemists to investigate ring-opening reactions and other transformations that can lead to new chemical entities. By understanding its reactivity, scientists can advance the field of synthetic organic chemistry and develop novel synthetic approaches.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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