316173-29-2

Basic information

• Product Name: (1S,2S,3S,4R)-Methyl 3-((R)-1-aMino-2-ethylbutyl)-4-(tert-butoxycarbonylaMino)-2-hydroxycyclopentanecarboxylate
• Synonyms: (1S,2S,3S,4R)-Methyl 3-((R)-1-aMino-2-ethylbutyl)-4-(tert-butoxycarbonylaMino)-2-hydroxycyclopentanecarboxylate;(1S,2S,3S,4R)-Methyl 3-((S)-1-aMino-2-ethylbutyl)-4-(tert-butoxycarbonylaMino)-2-hydroxycyclopentanecarboxylate;(1S,2S,3S,4R)-3-[(1S)-1-AMino-2-ethylbutyl]-4-[[(1,1-diMethylethoxy)carbonyl]aMino]-2-hydroxycyclopentanecarboxylic Acid Methyl Ester;Peramivir Intermediate 3;methyl (1S,2S,3S,4R)-3-[(1R)-1-amino-2-ethylbutyl]-2-hydroxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentane-1-carboxylate;Peramivir Intermediate III;4R)-Methyl 3-((R)-1-aMino-2-ethylbutyl)-4-(tert-butoxycarbonylaMino)-2-hydroxycyclopentanecarboxylate
• CAS NO: 316173-29-2
• Molecular Formula: C18H34N2O5
• Molecular Weight: 358.47296
• EINECS: 1308068-626-2
• Mol File: 316173-29-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 476.5±45.0 °C(Predicted)
• Appearance: /
• Density: 1.10±0.1 g/cm3 (20 oC 760 Torr), Calc.*
• PKA: 11.63±0.70(Predicted)
• CAS DataBase Reference: (1S,2S,3S,4R)-Methyl 3-((R)-1-aMino-2-ethylbutyl)-4-(tert-butoxycarbonylaMino)-2-hydroxycyclopentanecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,3S,4R)-Methyl 3-((R)-1-aMino-2-ethylbutyl)-4-(tert-butoxycarbonylaMino)-2-hydroxycyclopentanecarboxylate(316173-29-2)
• EPA Substance Registry System: (1S,2S,3S,4R)-Methyl 3-((R)-1-aMino-2-ethylbutyl)-4-(tert-butoxycarbonylaMino)-2-hydroxycyclopentanecarboxylate(316173-29-2)

Safety Data

• Hazardous Substances Data: 316173-29-2(Hazardous Substances Data)

Usage

Description

(1S,2S,3S,4R)-methyl 3-((R)-1-amino-2-ethylbutyl)-4-(tert-butoxycarbonylamino)-2-hydroxycyclopentanecarboxylate is a complex organic compound with a specific stereochemistry. It is characterized by its unique molecular structure, which includes a cyclopentane ring with various functional groups attached to it. (1S,2S,3S,4R)-methyl 3-((R)-1-amino-2-ethylbutyl)-4-(tert-butoxycarbonylamino)-2-hydroxycyclopentanecarboxylate is known for its role as an intermediate in the synthesis of pharmaceuticals.

Uses

Used in Pharmaceutical Industry:
(1S,2S,3S,4R)-methyl 3-((R)-1-amino-2-ethylbutyl)-4-(tert-butoxycarbonylamino)-2-hydroxycyclopentanecarboxylate is used as an intermediate in the synthesis of peramivir (P285500) for the treatment of influenza. Peramivir is a neuraminidase inhibitor that helps in preventing the spread of the influenza virus within the body, thus providing relief from the symptoms and shortening the duration of the illness.
Application Reason:
(1S,2S,3S,4R)-methyl 3-((R)-1-amino-2-ethylbutyl)-4-(tert-butoxycarbonylamino)-2-hydroxycyclopentanecarboxylate's specific stereochemistry and functional groups make it a suitable candidate for the synthesis of peramivir, a potent antiviral agent. Its role in the pharmaceutical industry is crucial, as it contributes to the development of effective treatments for influenza, a common and sometimes severe respiratory illness.

InChI:InChI=1S/C18H34N2O5/c1-7-10(8-2)14(19)13-12(20-17(23)25-18(3,4)5)9-11(15(13)21)16(22)24-6/h10-15,21H,7-9,19H2,1-6H3,(H,20,23)/t11-,12+,13+,14+,15+/m0/s1

Upstream product

• 97-96-1 2-Ethylbutyraldehyde 
• 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 

Downstream Products

• 229614-05-5 (-)-methyl (1S,2S,3R,4R)-3-[(1S)-1-(acetylamino)-2-ethylbutyl]-4-[(tert-butoxycarbonyl)amino]-2-hydroxycyclopentanecarboxylate 
• 229614-55-5 peramivir 
• 229615-05-8 (-)-methyl (1S,2S,3R,4R)-3-[(1S)-1-(acetylamino)-2-ethylbutyl]-4-amino-2-hydroxycyclopentanecarboxylate 
• 229614-56-6 peramivir 

Relevant articles and documents

Peramivir impurity A and impurity C, and preparation methods and application thereof

The invention discloses a peramivir impurity A and a peramivir impurity C with structures as shown in the specification. The invention also provides synthesis methods of the impurity A and the impurity C, and application of the impurity A and the impurity C as impurity reference substances in quality control of peramivir or a pharmaceutical composition thereof. The impurities can be stably prepared and supplied, and a basis is provided for related research and contrast. The peramivir impurity A and the peramivir impurity C disclosed by the invention have important significance in controlling peramivir raw material medicines and researching impurities of preparations of the peramivir raw material medicines.

Method for preparing key intermediate of anti-influenza drug peramivir

The invention discloses a method for preparing a key intermediate of an anti-influenza drug peramivir and belongs to the technical field of drug synthesis. The method includes taking a combination of cobalt and iron in a specific ratio as an additive and sodium borohydride as a reducing agent and reacting in an alcohol solvent. The method has the advantages of mild reaction conditions, simplicity and convenience in operation, low cost, high yield and high chiral purity.

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