Methyl (1R,4S)-4-Amino-2-cyclopentene-1-carboxylate (2S,3S)-2,3-Dihydroxybutanedioic Acid

CAS: 419563-23-8

Ref. TR-M220435

Product Information

• Name: Methyl (1R,4S)-4-Amino-2-cyclopentene-1-carboxylate (2S,3S)-2,3-Dihydroxybutanedioic Acid
• Synonyms: (2S,3S)-2,3-Dihydroxysuccinic acid - methyl (1R,4S)-4-amino-2-cyclopentene-1-carboxylate (1:1), (1R,4S)-METHYL 4-AMINOCYCLOPENT-2-ENECARBOXYLATE D-TARTRATE, (2S,3S)-2,3-Dihydroxybutanedioic acid methyl (1R,4S)-4-aminocyclopent-2-ene-1-carboxylate, Butanedioic acid, 2,3-dihydroxy- (2S,3S)-, compd. with methyl (1R,4S)-4-amino-2-cyclopentene-1-carboxylate (1:1)

Description

Applications Methyl (1R,4S)-4-Amino-2-cyclopentene-1-carboxylate (2S,3S)-2,3-Dihydroxybutanedioic Acid is an intermediate used in the synthesis of ent-Abacavir (A105015), which is 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.

• Brand: TRC

Chemical properties

• Molecular weight: 291.26
• Formula: C₇H₁₁NO₂·C₄H₆O₆
• Color/Form: Neat
• InChI: InChI=1S/C7H11NO2.C4H6O6/c1-10-7(9)5-2-3-6(8)4-5;5-1(3(7)8)2(6)4(9)10/h2-3,5-6H,4,8H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t5-,6+;1-,2-/m00/s1
• InChI key: InChIKey=XSEHIOOHMZAFCV-SCKHFGBISA-N
• SMILES: COC(=O)[C@H]1C=C[C@@H](N)C1.O=C(O)[C@@H](O)[C@H](O)C(=O)O