172720-97-7

Usage

Uses

1. Used in Pharmaceutical Industry:
Carbamic acid, [4-(hydroxymethyl)-2-cyclopenten-1-yl]-, 1,1-dimethylethyl is used as an intermediate in the synthesis of the HIV reverse transcriptase inhibitor Ziagen (also known as Abacavir). Its unique chemical structure allows it to be a crucial component in the development of this life-saving medication for patients suffering from HIV/AIDS.
2. Potential Applications in Drug Synthesis:
Given its structural properties, Carbamic acid, [4-(hydroxymethyl)-2-cyclopenten-1-yl]-, 1,1-dimethylethyl may also have potential applications in the synthesis of other pharmaceutical compounds. Its ability to form various chemical bonds and interact with different functional groups makes it a versatile building block for the development of new drugs targeting a range of diseases and conditions.

Upstream product

• 151792-53-9 tert-butyl (1R,4S)-(-)-3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 168960-19-8 (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene hydrochloride 
• 168683-02-1 (1S,4R)-(-)-methyl-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopent-2-ene-1-carboxylate 
• 4157-02-2 cis 2-cyclopentene 1,4-dibenzoate 
• 34619-03-9 tert-butyldicarbonate 
• 136522-35-5 (1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene 
• 130931-83-8 (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 216481-87-7 4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-cyclopentene-1-carboxylic acid 
• 162427-15-8 3-oxo-2-aza-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid tert-butyl ester 
• 7285-11-2 chloroform methanol 
• 33797-51-2 eschenmoser's salt 
• 189625-14-7 (2S,4R)-acetic acid 4-tert-butoxycarbonylaminocyclopent-2-enyl ester 

Downstream Products

• 136522-35-5 (1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene 
• 168960-19-8 (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene hydrochloride 
• 141271-12-7 (1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol 
• 121481-90-1 (+/-)-cis-(4-hydroxymethyl)cyclopent-2-en-1-ylamine 
• 77745-28-9 cis-4-Aminocyclopent-2-enemethanol Hydrochloride 
• 168960-19-8 (1S,4R)-1-amino-4-hydroxymethyl-2-cyclopentene hydrochloride 
• 1233843-46-3 C₆H₁₁NO*ClH 
• 220285-03-0 [(1R,3S)-3-(6-amino-9H-purin-9-yl)cyclopentyl]methanol 
• 158799-91-8 (1R,cis)-4-(6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol 
• 112966-73-1 [(1R,3S)-3-(6-amino-9H-purin-9-yl)cyclopentyl]methanol 
• 918492-98-5 (1α,4α)-4-(6-Chloro-9H-purin-9-yl)-2-cyclopentenyl-carbinol 

Relevant academic research and scientific papers

The Synthesis of trans-Carbovir via the Ramberg-Baecklund Reaction

A novel Ramberg-Baecklund approach to the synthesis of 1-amino-4-substituted cyclopentenes is described and applied to prepare the trans-isomer of the carbocyclic nucleoside carbovir.

Diastereoselective Diboration of Cyclic Alkenes: Application to the Synthesis of Aristeromycin

The Pt-catalyzed diboration of cyclic alkenes is extended to unsaturated heterocycles and bicyclic compounds and can be accomplished in a diastereoselective fashion. The optimal procedures, substrate scope, and diastereoselectivity were investigated, and examples employing both homogeneous and heterogeneous catalysis were examined. Lastly, application to the construction of the nucleoside analog (±)-aristeromycin was conducted.

Discovery of Pyrazolocarboxamides as Potent and Selective Receptor Interacting Protein 2 (RIP2) Kinase Inhibitors

Herein we report the discovery of pyrazolocarboxamides as novel, potent, and kinase selective inhibitors of receptor interacting protein 2 kinase (RIP2). Fragment based screening and design principles led to the identification of the inhibitor series, and X-ray crystallography was used to inform key structural changes. Through key substitutions about the N1 and C5 N positions on the pyrazole ring significant kinase selectivity and potency were achieved. Bridged bicyclic pyrazolocarboxamide 11 represents a selective and potent inhibitor of RIP2 and will allow for a more detailed investigation of RIP2 inhibition as a therapeutic target for autoinflammatory disorders.

A Mitsunobu reaction to functionalized cyclic and bicyclic N-arylamines

The scope of an unexpected Mitsunobu cyclisation to prepare N-arylated Fsp3-enriched azacycles was investigated. In the current study, we have identified whether a pKa-dependent Mitsunobu cyclodehydration or a pKa-independent Mitsunobu intramolecular reaction was in operation. A Mitsunobu reaction, creating a leaving group, followed by intramolecular nucleophilic displacement was determined to be the dominant pathway.

Optical pure amino alcohol hydrochloride preparation method

The invention relates to a preparation method for optically pure aminoalcohol hydrochloride. The optically pure aminoalcohol hydrochloride is any one selected from optically pure aminoalcohol hydrochloride 1 and optically pure aminoalcohol hydrochloride 2 and is prepared by subjecting a compound 4 to an esterification ring-opening reaction, an amino protection reaction, an ester reduction reaction and a deprotection salt forming reaction. The optically pure aminoalcohol hydrochloride 1 or optically pure aminoalcohol hydrochloride 2 prepared in the invention can be directly used for synthesis of abacavir and carbovir. The preparation method provided by the invention has the advantages of high product optical purity, stable product quality, high product yield, a small amount of environmental pollution, low production cost, easy industrialization, etc.

Squarate-based carbocyclic nucleosides: Syntheses, computational analyses and anticancer/antiviral evaluation

Squaric acid and its derivatives are versatile synthons and have demonstrated applications in medicinal chemistry, notably as non-classical bioisosteric replacements for functional groups such as carboxylic acids, alpha-amino acids, urea, guanidine, peptide bonds and phosphate/pyrophosphate linkages. Surprisingly, no reports have appeared concerning its possible application as a nucleobase substitute in nucleosides. A preliminary investigation of such an application is reported herein. 3-Amino-4-((1R,4S)-4-(hydroxymethyl)cyclopent-2-en-1-yl)amino-cyclobut-3-ene-1,2-dione, 3-((1R,4S)-4-(hydroxymethyl)cyclopent-2-en-1-yl)amino-4-methoxycyclobut-3-ene-1,2-dione, and 3-hydroxy-4-((1R,4S)-4-(hydroxymethyl)cyclopent-2-en-1-yl)amino-cyclobut-3-ene-1,2-dione sodium salt were synthesized. Computational analyses of their structures and preliminary antitumor and antiviral screening results are reported.

An expedient synthesis of oxazepino and oxazocino quinazolines

A synthetic route to a new class of privileged tri- and tetra-cyclic quinazolines containing a medium-sized ring is reported. An expedient synthetic route involving nucleophilic aromatic substitution, and sequential Niementowski and BOP-mediated ring clos

Synthesis of novel N-cyclopentenyl-lactams using the Aubé reaction

A novel and convenient method utilizing the Aubé reaction to access a new class of compounds that are similar to carbocyclic nucleosides is reported. The azido alcohol derived from Vince lactam undergoes the Aubé reaction with various cyclic ketones to gi

LUPEOL-TYPE TRITERPENE DERIVATIVES AS ANTIVIRALS

The invention relates to novel lupeol-type triterpene derivatives and related compounds, and pharmaceutical compositions useful for therapeutic treatment of viral diseases and particularly HIV mediated diseases.

Palladium(0)/indium iodide-mediated allylations of electrophiles generated from the hydrolysis of Eschenmoser's salt: one-pot preparation of diverse carbocyclic scaffolds

A formyl equivalent was generated in situ from Eschenmoser's salt in aqueous THF and was reacted with an allylindium species. Acylnitroso-derived hetero-Diels-Alder adducts and related allyl acetates were shown to be substrates for Pd(0)/InI-mediated allylations of formaldehyde-related species to provide homoallylic alcohols. Hydroxymethyl groups were installed with regio- and diastereocontrol to provide relevant disubstituted carbocyclic scaffolds. Enantiopure anti-disubstituted cyclopentene products were prepared from a chiral allyl acetate.