CAS 136522-35-5

(1S,4R)-4-Amino-2-cyclopentene-1-methanol

Description:

(1S,4R)-4-Amino-2-cyclopentene-1-methanol is a chiral organic compound characterized by its unique cyclopentene structure, which includes an amino group and a hydroxymethyl group. The presence of the amino group contributes to its potential as a building block in pharmaceutical synthesis, while the hydroxymethyl group can participate in various chemical reactions, such as nucleophilic substitutions. The specific stereochemistry indicated by the (1S,4R) configuration suggests that the compound exhibits optical activity, making it relevant in the study of enantiomers and their biological activities. This compound may also display interesting reactivity due to the strained cyclopentene ring, which can influence its stability and reactivity patterns. Its applications could extend to medicinal chemistry, where such compounds are often explored for their potential therapeutic effects. Overall, (1S,4R)-4-Amino-2-cyclopentene-1-methanol represents a valuable structure in organic synthesis and medicinal research, with its properties largely dictated by its functional groups and stereochemistry.

Formula: C₆H₁₁NO

InChI: InChI=1S/C6H11NO/c7-6-2-1-5(3-6)4-8/h1-2,5-6,8H,3-4,7H2/t5-,6+/m1/s1

InChI key: InChIKey=UXKZFJDNFBNQHE-RITPCOANSA-N

SMILES: C(O)[C@H]1C[C@@H](N)C=C1

Synonyms:

• (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

((1S,4R)-4-Aminocyclopent-2-en-1-yl)methanol

CAS: 136522-35-5

Formula: C₆H₁₁NO

Molecular weight: 113.1576

Ref: IN-DA0011YE

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

Controlled Product

CAS: 136522-35-5

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.

Formula: C₆H₁₁NO·C₁₈H₁₄O₈

Color and Shape: Neat

Molecular weight: 471.46

Ref: TR-A603643

(1S,4R)-4-Amino-2-cyclopentene-1-methanol

Controlled Product

CAS: 136522-35-5

Formula: C₆H₁₁NO

Color and Shape: Neat

Molecular weight: 113.158

Ref: TR-A603935