N-​[(1R,​4S)​-​4-​(Hydroxymethyl)​-​2-​cyclopenten-​1-​yl]​-carbamic Acid 1,​1-​Dimethylethyl Ester

CAS: 168960-18-7

Ref. TR-H942223

Product Information

• Name: N-​[(1R,​4S)​-​4-​(Hydroxymethyl)​-​2-​cyclopenten-​1-​yl]​-carbamic Acid 1,​1-​Dimethylethyl Ester
• Synonyms: (1R-cis)-[4-(Hydroxymethyl)-2-cyclopenten-1-yl]-carbamic Acid 1,1-Dimethylethyl Ester, [(1R,4S)-4-(Hydroxymethyl)-2-cyclopenten-1-yl]-carbamic Acid 1,1-Dimethylethyl Ester, Tert-Butyl Cis-[4(S)-(Hydroxymethyl)Cyclopent-2-En-1(R)-Yl]Carbamate, Carbamic acid, [(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]-, 1,1-, Tert-Butyl (1R,4S)-4-(Hydroxymethyl)Cyclopent-2-Enylcarbamate

Description

Applications N-​[(1R,​4S)​-​4-​(Hydroxymethyl)​-​2-​cyclopenten-​1-​yl]​-carbamic 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.

• Brand: TRC

Chemical properties

• Molecular weight: 213.27
• Formula: C₁₁H₁₉NO₃
• Color/Form: Yellow Oil
• InChI: InChI=1S/C11H19NO3/c1-11(2,3)15-10(14)12-9-5-4-8(6-9)7-13/h4-5,8-9,13H,6-7H2,1-3H3,(H,12,14)/t8-,9+/m1/s1
• InChI key: InChIKey=MVIWPMBRXBNBDX-BDAKNGLRSA-N
• SMILES: CC(C)(C)OC(=O)N[C@H]1C=C[C@@H](CO)C1