(1S,4R)-4-Amino-2-cyclopentene-1-methanol (-)-Dibenzoyl-L-tartaric Acid

CAS: 136522-35-5

Ref. TR-A603643

Produktinformation

• Name: (1S,4R)-4-Amino-2-cyclopentene-1-methanol (-)-Dibenzoyl-L-tartaric Acid
• Synonyme: (1S,4R)-4-Amino-2-Cyclopentene-1-Methanol, (1s,Cis)-4-amino-2-cyclopentene-1-methanol, 2-Cyclopentene-1-methanol, 4-amino-, (1S,4R)-, 2-Cyclopentene-1-methanol, 4-amino-, (1S-cis)-, Aminocarbinol, [(1S,4R)-4-aminocyclopent-2-en-1-yl]methanol

Beschreibung

Applications (1S,4R)-4-Amino-2-cyclopentene-1-methanol (-)-Dibenzoyl-L-tartaric Acid 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.

• Marke: TRC

Chemische Eigenschaften

• Molekulargewicht: 471.46
• Formel: C₆H₁₁NO·C₁₈H₁₄O₈
• Farbe/Form: Neat
• InChl: InChI=1S/C18H14O8.C6H11NO/c19-15(20)13(25-17(23)11-7-3-1-4-8-11)14(16(21)22)26-18(24)12-9-5-2-6-10-12;7-6-2-1-5(3-6)4-8/h1-10,13-14H,(H,19,20)(H,21,22);1-2,5-6,8H,3-4,7H2/t13-,14-;5-,6+/m11/s1
• InChI Key: InChIKey=JRTMUXDUCOLQNQ-ZMFJZPHJSA-N
• SMILES: N[C@H]1C=C[C@@H](CO)C1.O=C(O[C@@H](C(=O)O)[C@@H](OC(=O)c1ccccc1)C(=O)O)c1ccccc1