213316-20-2

Usage

Uses

Used in Organic Synthesis:
1-TERT-BUTOXYCARBONYLAMINO-CYCLOPENT-3-ENECARBOXYLIC ACID is used as a protecting group for amines in organic synthesis, ensuring the selective reaction of other functional groups without affecting the amine.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 1-TERT-BUTOXYCARBONYLAMINO-CYCLOPENT-3-ENECARBOXYLIC ACID is used as a reagent in the formation of peptide bonds, which are crucial for the synthesis of various drugs and biochemical compounds.
Used in Medicinal Chemistry:
1-TERT-BUTOXYCARBONYLAMINO-CYCLOPENT-3-ENECARBOXYLIC ACID is utilized in medicinal chemistry for the modification and protection of functional groups in organic molecules, contributing to the development of new drugs and therapeutic agents.
Used in Drug Development:
This chemical is employed in drug development for its unique structure and properties, making it a valuable tool in the creation of various organic compounds and materials with potential therapeutic applications.
Used in Biochemical Compounds Production:
1-TERT-BUTOXYCARBONYLAMINO-CYCLOPENT-3-ENECARBOXYLIC ACID is used in the production of biochemical compounds, where its ability to form peptide bonds is essential for the synthesis of bioactive molecules with specific functions in biological systems.

Upstream product

• 207729-00-8 ethyl 1-((tert-butoxycarbonyl)amino)cyclopent-3-ene-1-carboxylate 
• 952193-59-8 C₁₅H₂₄N₂O₂ 
• 952193-55-4 (2R)-5,5-diallyl-3,6-diethoxy-2,5-dihydro-2-isopropylpyrazine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 199532-88-2 ethyl 1-aminocyclopent-3-ene-1-carboxylate 
• 84646-68-4 Dimethyl 3-cyclopentene-1,1-dicarboxylate 
• 288303-88-8 1-tert-butoxycarbonylamino-cyclopent-3-enecarboxylic acid methyl ester 

Downstream Products

• 354526-96-8 N-[(1-(tert-butoxycarbonylamino)-cyclopent-3-enyl)carbonyl]-L-phenylalanine methyl ester 
• 675833-87-1 [1-(2'-tert-butylsulfamoyl-3-fluoro-biphenyl-4-ylcarbamoyl)-cyclopent-3-enyl]-carbamic acid tert-butyl ester 
• 869786-63-0 1-(tert-butoxycarbonylamino)-cyclopent-3-ene-1-carboxylic acid N-[3-methyl-4-(3-oxo-morpholin-4-yl)-phenyl]-amide 

Relevant academic research and scientific papers

Helical structures of cyclopentenebased α,α-disubstituted a-amino acid homopeptides

The cyclopentene-based α,α-disubstituted a-amino acid Ac5c= and its homopeptides, up to nonapeptides, were synthesized. The side-chain cyclopentene was expected to become symmetric, the Ca-carbon to be puckered, and other Cβ, Cβ', C, C-carbons to be coplanar. As expected, side-chain cyclopentene conformations became symmetric and Ca-carbons were puckered. Conformational studies using FT-IR absorption, 1H NMR spectra, and X-ray crystallographic analyses revealed that Ac5c= homopeptides did not form a planar conformation, but assumed a 310-helical structure, similar to cyclopentane-based α,α-disubstituted a-amino acid homopeptides.

Microwave assisted synthesis of spiro-2,5-diketopiperazines

A general and efficient method for the synthesis of spiro-2,5-diketopiperazines (spiro-DKPs) is described. Cyclization of Boc-protected dipeptides containing spiro-amino acids by microwave assisted heating in water furnished the corresponding spiro-DKPs. The spiro-amino acids were prepared by combining stereoselective alkylation reactions using the Sch?llkopf methodology for amino acid construction with Grubbs ring-closing metathesis (RCM) methodology using ruthenium complexes. The RCM reactions and all subsequent transformations to the spiro-DKPs were run with microwave assisted heating, resulting in high yields and short reaction times for all steps.

Synthesis of isoxazoline-substituted symmetrical diketopiperazines

A synthesis of racemic isoxazoline substituted symmetrical diketopiperazines has been achieved by twice utilizing a diastereoselective 1,3-dipolar cycloaddition step - mediated by intermolecular hydrogen-bonds between the Boc-NH of 2 and the requisite nitrile oxide (RCN+-O-) - to control alkene face selectivity. Dehydrative cyclization of the amide-linked amino acid 6 delivered diketopiperazine 8.

Diastereoselective Solid-Phase Synthesis of Novel Hydantoin- and Isoxazoline-Containing Heterocycles

Exploiting 1,3-dipolar cycloaddition and carbanilide cyclization transformations, we have prepared novel spirocyclic isoxazoloimidazolidinedione heterocycles of generalized structures II and III on solid phase starting from Merrifield resin. Cyclopentanoid isoxazoloimidazolidinedione II was obtained with complete diastereoselectivity, and cyclopropanoid isoxazoloimidazolidinedione III was obtained as an ≈ 2:1 mixture of diastereomers.