151792-53-9

Basic information

• Product Name: (6R,7S)-2-BOC-2-AZA-BICYCLO[2.2.1]HEPT-5-EN-3-ONE
• Synonyms: (6R,7S)-2-BOC-2-AZA-BICYCLO[2.2.1]HEPT-5-EN-3-ONE;(1R,4S)-tert-butyl 3-oxo-2-aza-bicyclo[2.2.1]hept-5-ene-2-carboxylate;2-Azabicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 3-oxo-,1,1-diMethylethyl ester, (1R,4S)-
• CAS NO: 151792-53-9
• Molecular Formula: C₁₁H₁₅NO₃
• Molecular Weight: 209.25
• Mol File: 151792-53-9.mol
• Article Data: 25

Chemical Properties

• Melting Point: 85.0-86.5 °C
• Boiling Point: 339.8±31.0 °C(Predicted)
• Appearance: /
• Density: 1 +-.0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: -2.32±0.20(Predicted)
• CAS DataBase Reference: (6R,7S)-2-BOC-2-AZA-BICYCLO[2.2.1]HEPT-5-EN-3-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (6R,7S)-2-BOC-2-AZA-BICYCLO[2.2.1]HEPT-5-EN-3-ONE(151792-53-9)
• EPA Substance Registry System: (6R,7S)-2-BOC-2-AZA-BICYCLO[2.2.1]HEPT-5-EN-3-ONE(151792-53-9)

Safety Data

• Hazardous Substances Data: 151792-53-9(Hazardous Substances Data)

Usage

Uses

(1R,?4S)?-3-?Oxo-2-?azabicyclo[2.2.1]?hept-?5-?ene-?2-?carboxylic acid 1,?1-?Dimethylethyl Ester is an intermediate in synthesizing ent-Abacavir (Abacavir EP Impurity A) (A105015), an enatiomer of Abacavir (A105000). Abacavir is a carbocyclic 2''-deoxyguanosine nucleoside reverse transcriptase inhibitor and an anti-HIV drug used to treat HIV infection (1). Intracellular enzymes convert Abacavir to its active form, carbovir-triphosphate (CBV-TP), which then selectively inhibits HIV reverse transcriptase by incorporating into viral DNA (2). Abacavir is metabolized in the liver by uridine diphosphate glucuronyltransferase and alcohol dehydrogenase resulting in inactive glucuronide and carboxylate metabolites, respectively.

Upstream product

• 162427-15-8 3-oxo-2-aza-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid tert-butyl ester 
• 168773-55-5 (1R,4S,6S)-6-Hydroxy-2-(p-methoxybenzyl)-2-azabicyclo<2.2.1>-3-heptanone 
• 168773-56-6 (1R,4S,6R)-6-Iodo-2-(p-methoxybenzyl)-2-azabicyclo<2.2.1>-3-heptanone 
• 168773-48-6 (1R,4S,6S)-6-(tert-Butyldimethylsiloxy)-2-azabicyclo<2.2.1>-3-heptanone 
• 49805-30-3 2-azabicyclo[2.2.1.]hept-5-en-3-one 
• 24424-99-5 di-tert-butyl dicarbonate 
• 79200-56-9 (-)-2-azabicyclo[2.2.1]hept-5-en-3-one 
• 134003-03-5 (+)-2-Azabicyclo<2.2.1>heptan-3-one 
• 49805-30-3 racemic 2-azabicyclo[2.2.1]hept-5-en-3-one 
• 168773-38-4 (5S,6R)-5-<(tert-Butyldimethylsilyl)oxy>-6-<(benzyloxy)methyl>-2-piperidinone 
• 168960-17-6 (1R,4S)-2-(p-Methoxybenzyl)-2-azabicyclo<2.2.1>-5-hepten-3-one 
• 168773-36-2 (5S,6R)-5-Hydroxy-6-<(benzyloxy)methyl>-2-piperidinone 
• 168773-43-1 (5S,6R)-1-(p-Methoxybenzyl)-5-<(tert-butyldimethylsilyl)oxy>-6-<(benzyloxy)methyl>-2-piperidinone 
• 168773-58-8 Trifluoro-methanesulfonic acid (1R,4S)-2-(4-methoxy-benzyl)-3-oxo-2-aza-bicyclo[2.2.1]hept-5-en-6-yl ester 

Downstream Products

• 151907-79-8 (1S-cis)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-cyclopentene-1-carboxylic acid 
• 664341-72-4 (1S,4R)-1-tert-butoxycarbonylamino-4-hydroxymethylcyclopentane 
• 123880-25-1 (1R,2R,3R,5R)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol 
• 161660-94-2 (1R,3S)-3-((tert-butoxycarbonyl)amino)cyclopentane-1-carboxylic acid 
• 153011-43-9 (1S,cis)-tert-butyl N-[4-(hydroxymethyl)-2-cyclopenten-1-yl]carbamate 
• 1450975-28-6 (+)-(1R,2S,5R)-5-(hydroxymethyl)cyclopent-3-ene-1,2-diyl dibenzoate 
• 1007125-09-8 (-)-(1R,2S,3R,5R)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diyl dibenzoate hydrochloride 
• 1007125-08-7 (-)-(1R,2S,3R,5R)-3-((tert-butoxycarbonyl)amino)-5-(hydroxymethyl)cyclopentane-1,2-diyl dibenzoate 
• 1007125-07-6 tert-butyl (1R,4S,5R,6S)-5,6-bis(benzoyloxy)-3-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate 
• 1350898-63-3 (1R,4R,6S)-tert-butyl 6-(((4-methoxyphenyl)amino)methyl)3-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate 
• 1312161-65-1 C₁₁H₁₇NO₄ 
• 298716-03-7 (1R,4R)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylic acid 
• 168958-19-8 methyl (1R,4R)-4-(tert-butoxycarbonylamino)cyclopent-2-ene-1-carboxylate 
• 168683-02-1 (1S,4R)-(-)-methyl-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopent-2-ene-1-carboxylate 

Relevant articles and documents

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