CAS 229177-52-0

2-Cyclopentene-1-methanol, 4-amino-, (1S,4R)-, (2S,3S)-2,3-dihydroxybutanedioate (1:1) (salt)

Description:

2-Cyclopentene-1-methanol, 4-amino-, (1S,4R)-, (2S,3S)-2,3-dihydroxybutanedioate (1:1) (salt) is a complex organic compound characterized by its unique stereochemistry and functional groups. The presence of a cyclopentene ring indicates it has unsaturation, contributing to its reactivity and potential applications in organic synthesis. The amino group suggests it may participate in various chemical reactions, such as nucleophilic substitutions or coupling reactions. The dihydroxybutanedioate moiety introduces additional hydroxyl groups, enhancing its solubility in polar solvents and potentially influencing its biological activity. This compound's salt form indicates it may exist as an ionic species, which can affect its stability and interaction with other molecules. Overall, the combination of these features suggests that this substance could be of interest in medicinal chemistry or as a building block in the synthesis of more complex molecules. Its specific stereochemistry may also play a crucial role in determining its biological properties and interactions.

Formula: C₆H₁₁NO·C₄H₆O₆

InChI: InChI=1S/C6H11NO.C4H6O6/c7-6-2-1-5(3-6)4-8;5-1(3(7)8)2(6)4(9)10/h1-2,5-6,8H,3-4,7H2;1-2,5-6H,(H,7,8)(H,9,10)/t5-,6+;1-,2-/m10/s1

InChI key: InChIKey=LTSTZOJHLZNDFG-ZGMNSGLWSA-N

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

Synonyms:

• (1S,4R)-4-Amino-2-cyclopentene-1-methanol (2S,3S)-2,3-dihydroxybutanedioate (1:1) salt
• (1S-cis)-4-Amino-2-cyclopentene-1-menthanol D-hydrogen tatrate
• 2-Cyclopentene-1-methanol, 4-amino-, (1S,4R)-, (2S,3S)-2,3-dihydroxybutanedioate (1:1) (salt)
• [(1S,4R)-4-aminocyclopent-2-en-1-yl]methanol 2,3-dihydroxybutanedioate (1:1)

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

CAS: 229177-52-0

Formula: C₁₀H₁₇NO₇

Purity: 95%

Color and Shape: Solid

Molecular weight: 263.2445

Ref: IN-DA002LHU

(1S-cis)-4-Amino-2-cyclopentene-1-methanol D-hydrogen tatrate

CAS: 229177-52-0

Ref: 7W-GK2535

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

Controlled Product

CAS: 229177-52-0

Impurity Abacavir - In House Impurity
Applications (1S,4R)-cis-4-Amino-2-cyclopentene-1-methanol D-Tartrate (Abacavir - In House Impurity) is an intermediate of Abacavir (A104990). 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.
References (1) Jackson, A., et al.: Antivir Ther. 17, 19 (2012) (2) Yuen, G. J., et al.: Clin Pharmacokinet. 47, 351 (2008)

Formula: C₆H₁₁NO·C₄H₆O₆

Color and Shape: Neat

Molecular weight: 263.24

Ref: TR-A603640

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

CAS: 229177-52-0

Formula: C₆H₁₁NOC₄H₆O₆

Molecular weight: 113.16 : 150.09

Ref: ST-EA-CP-A1055