229614-05-5

Basic information

• Product Name: (1S,2S,3R,4R)-Methyl 3-((R)-1-acetaMido-2-ethylbutyl)-4-(tert-butoxycarbonylaMino)-2-hydroxycyclopentanecarboxylate
• Synonyms: (1S,2S,3R,4R)-Methyl 3-((R)-1-acetaMido-2-ethylbutyl)-4-(tert-butoxycarbonylaMino)-2-hydroxycyclopentanecarboxylate;(S)-1-(2-nitrobenzyl)-5-oxopyrrolidine-2-carboxylic acid;(1S,2S,3R,4R)-METHYL 3-((S)-1-ACETAMIDO-2-ETHYLBUTYL)-4-(TERT-BUTOXYCARBONYLAMINO)-2-HYDROXYCYCLOPENTANECARBOXYLATE
• CAS NO: 229614-05-5
• Molecular Formula: C20H36N2O6
• Molecular Weight: 400.50964
• Mol File: 229614-05-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 562.6±50.0 °C(Predicted)
• Appearance: /
• Density: 1.11±0.1 g/cm3(Predicted)
• PKA: 11.56±0.70(Predicted)
• CAS DataBase Reference: (1S,2S,3R,4R)-Methyl 3-((R)-1-acetaMido-2-ethylbutyl)-4-(tert-butoxycarbonylaMino)-2-hydroxycyclopentanecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,3R,4R)-Methyl 3-((R)-1-acetaMido-2-ethylbutyl)-4-(tert-butoxycarbonylaMino)-2-hydroxycyclopentanecarboxylate(229614-05-5)
• EPA Substance Registry System: (1S,2S,3R,4R)-Methyl 3-((R)-1-acetaMido-2-ethylbutyl)-4-(tert-butoxycarbonylaMino)-2-hydroxycyclopentanecarboxylate(229614-05-5)

Safety Data

• Hazardous Substances Data: 229614-05-5(Hazardous Substances Data)

Usage

Description

(1S,2S,3R,4R)-methyl 3-((R)-1-Acetamido-2-ethylbutyl)-4-(tert-butoxycarbonylamino)-2-hydroxycyclopentanecarboxylate is a complex organic compound with a unique molecular structure. It is characterized by its chiral centers at the 1S, 2S, 3R, and 4R positions, which contribute to its specific biological activities. The compound features an acetamido group, a tert-butoxycarbonyl group, and a hydroxyl group, which may be involved in various interactions with biological targets.

Uses

1. Used in Pharmaceutical Industry:
(1S,2S,3R,4R)-methyl 3-((R)-1-Acetamido-2-ethylbutyl)-4-(tert-butoxycarbonylamino)-2-hydroxycyclopentanecarboxylate is used as a key intermediate in the synthesis of novel pharmaceutical compounds for various therapeutic applications. Its unique structure and functional groups make it a promising candidate for the development of new drugs targeting specific biological pathways.
2. Used in Drug Delivery Systems:
The compound can be utilized in the design and development of drug delivery systems, particularly for targeted drug delivery. Its functional groups can be exploited to attach drug molecules or other therapeutic agents, enabling controlled and specific release at the site of action.
3. Used in Chemical Research:
(1S,2S,3R,4R)-methyl 3-((R)-1-Acetamido-2-ethylbutyl)-4-(tert-butoxycarbonylamino)-2-hydroxycyclopentanecarboxylate can be employed as a research tool in chemical and biological studies. Its unique structure and chirality make it an interesting subject for investigations into stereochemistry, molecular recognition, and biological activity.
4. Used in the Preparation of Bifunctional Conjugates:
Similar to the use of 2,3-Diethylpiperazine in the preparation of bifunctional zanamivir conjugates, (1S,2S,3R,4R)-methyl 3-((R)-1-Acetamido-2-ethylbutyl)-4-(tert-butoxycarbonylamino)-2-hydroxycyclopentanecarboxylate can be used as a reagent in the synthesis of bifunctional conjugates with enhanced therapeutic properties. These conjugates could potentially combine the benefits of multiple drugs or therapeutic agents, leading to improved treatment outcomes.

InChI:InChI=1S/C20H36N2O6/c1-8-12(9-2)16(21-11(3)23)15-14(22-19(26)28-20(4,5)6)10-13(17(15)24)18(25)27-7/h12-17,24H,8-10H2,1-7H3,(H,21,23)(H,22,26)/t13-,14+,15+,16?,17+/m0/s1

Upstream product

• 168683-02-1 (1S,4R)-(-)-methyl-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopent-2-ene-1-carboxylate 
• 229613-83-6 (–)-methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride 
• 79200-56-9 (-)-2-azabicyclo[2.2.1]hept-5-en-3-one 
• 229613-93-8 (+)-methyl (3aR,4R,6S,6aS)-4-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropyl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylate 
• 108-24-7 acetic anhydride 
• 1988779-13-0 (1S,2S,3S,4R)-methyl 3-((S)-1-amino-2-ethylbutyl)-4-(tert-butoxycarbonylamino)-2-hydroxycyclopentanecarboxylate 

Downstream Products

• 229615-05-8 (-)-methyl (1S,2S,3R,4R)-3-[(1S)-1-(acetylamino)-2-ethylbutyl]-4-amino-2-hydroxycyclopentanecarboxylate 
• 1352062-19-1 C₁₄H₂₆N₂O₄*ClH 

Relevant articles and documents

Peramivir Phosphonate Derivatives as Influenza Neuraminidase Inhibitors

Peramivir is a potent neuraminidase (NA) inhibitor for treatment of influenza infection by intravenous administration. By replacing the carboxylate group in peramivir with a phosphonate group, phosphono-peramivir (6a), the dehydration and deoxy derivatives (7a and 8a) as well as their corresponding monoalkyl esters are prepared from a pivotal intermediate epoxide 12. Among these phosphonate compounds, the dehydration derivative 7a that has a relatively rigid cyclopentene core structure exhibits the strongest inhibitory activity (IC50 = 0.3-4.1 nM) against several NAs of wild-type human and avian influenza viruses (H1N1, H3N2, H5N1, and H7N9), although the phosphonate congener 6a is unexpectedly less active than peramivir. The inferior binding affinity of 6a is attributable to the deviated orientations of its phosphonic acid and 3-pentyl groups in the NA active site as inferred from the NMR, X-ray diffraction, and molecular modeling analyses. Compound 7a is active to the oseltamivir-resistant H275Y strains of H1N1 and H5N1 viruses (IC50 = 73-86 nM). The phosphonate monoalkyl esters (6b, 6c, 7b, 7c, 8b, and 8c) are better anti-influenza agents (EC50 = 19-89 nM) than their corresponding phosphonic acids (EC50 = 50-343 nM) in protection of cells from the viral infection. The phosphonate monoalkyl esters are stable in buffer solutions (pH 2.0-7.4) and rabbit serum; furthermore, the alkyl group is possibly tuned to attain the desired pharmacokinetic properties.

Facile synthesis of the neuraminidase inhibitor peramivir

An improved and convenient synthetic route for the synthesis of peramivir has been developed with a total 34% yield. The process was improved from previous methods in three key reaction steps including 1,3-dipolar cycloaddition, reductive ring cleavage of

Substituted cyclopentane and cyclopentene compounds useful as neuraminidase inhibitors

Compounds I-III wherein U is CH, O, or S; Z is mono- or di-substituted carbon; R is (CH2)nCO2H, (CH2)nSO3H, (CH2)nPO3H2, (CH2)nNO2, CH(SCH3)3, esters; R1 is H, hydroxyalkyl, aminoalkyl, alkoxyalkyl; RR1 is O; n is 0-4; R2, R3 is H, hydroxyalkyl, aminoalkyl, alkoxyalkyl, haloalkyl; R4 is (CH2)nOH, (CH2)nNH2, substituted alkyl were prepd. as neuraminidase inhibitors. Thus, (1R,3R,4R,1′S)-(?)-(1′-acetylamino-2 ′-ethyl)butyl-4-(aminoimino)methylaminocyclopentan-1-carboxylic acid was prepd. and tested in vitro as neuraminidase inhibitor (IC501μM).