229177-52-0

Basic information

• Product Name: (1S-cis)-4-Amino-2-cyclopentene-1-methanol D-hydrogen tatrate
• Synonyms: (1S,4R)-4-Amino-2-cyclopentene-1-methanol (2S,3S)-2,3-dihydroxybutanedioate (1:1) salt;(1S-cis)-4-Amino-2-cyclopentene-1-methanol D-hydrogen tatrate;(1S,4R)-4-AMino-2-cyclopentene-1-Methanol tartrate;(1S,4R)-4-aMino-2-cyclopentene-1-Methanol D-Tartarate;(1S,4R)-cis-4-AMino-2-cyclopentene-1-Methanol (2S,3S)-2,3-Dihydroxybutanedioate;(1S,4R)-cis-4-AMino-2-cyclopentene-1-Methanol D-Tartrate;(1S-cis)-4-AMino-2-cyclopentene-1-Methanol D-Tartrate;((1S,4R)-4-Aminocyclopent-2-en-1-yl)methanol (2S,3S)-2,3-dihydroxysuccinate
• CAS NO: 229177-52-0
• Molecular Formula: (x)C₄H₆O₆*C₆H₁₁NO
• Molecular Weight: 263.244
• EINECS: 418-530-1
• Mol File: 229177-52-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 399.3 °C at 760 mmHg
• Flash Point: 209.4 °C
• Appearance: /
• Vapor Pressure: 4.93E-08mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
• CAS DataBase Reference: (1S-cis)-4-Amino-2-cyclopentene-1-methanol D-hydrogen tatrate(CAS DataBase Reference)
• NIST Chemistry Reference: (1S-cis)-4-Amino-2-cyclopentene-1-methanol D-hydrogen tatrate(229177-52-0)
• EPA Substance Registry System: (1S-cis)-4-Amino-2-cyclopentene-1-methanol D-hydrogen tatrate(229177-52-0)

Safety Data

• Hazardous Substances Data: 229177-52-0(Hazardous Substances Data)

Usage

Description

(1S-cis)-4-Amino-2-cyclopentene-1-methanol D-hydrogen tartrate, also known as Abacavir intermediate, is a white solid chemical compound that serves as an essential intermediate in the synthesis of Abacavir, an antiviral therapeutic nucleoside analog. It plays a crucial role in the development of antiviral medications, particularly those targeting human immunodeficiency virus (HIV).

Uses

Used in Pharmaceutical Industry:
(1S-cis)-4-Amino-2-cyclopentene-1-methanol D-hydrogen tartrate is used as an intermediate compound for the synthesis of Abacavir, an antiviral drug. Abacavir is effective against HIV and is commonly used in combination with other antiretroviral medications to treat HIV-1 infection. The compound's role in the pharmaceutical industry is to facilitate the production of life-saving medications for patients suffering from HIV.
Used in Antiviral Research:
In addition to its application in the pharmaceutical industry, (1S-cis)-4-Amino-2-cyclopentene-1-methanol D-hydrogen tartrate is also utilized in antiviral research. Researchers use this compound to study the mechanisms of action of nucleoside analogs and their potential applications in the development of new antiviral drugs. This research contributes to the ongoing efforts to combat viral infections and improve public health.
Used in Drug Synthesis:
(1S-cis)-4-Amino-2-cyclopentene-1-methanol D-hydrogen tartrate is used as a key component in the synthesis of various antiviral drugs. Its chemical properties make it an ideal candidate for the development of new medications that can effectively target and neutralize viral pathogens. This application is vital in the ongoing battle against emerging and existing viral threats, ensuring the continuous advancement of medical treatments and therapies.

InChI:InChI=1/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

Synthetic route

D-tartaric acid (147-71-7) + (1S,4R)-methyl 4-aminocyclopent-2-enecarboxylate L-hydrogen tartrate → ((1S,4R)-4-aminocyclopent-2-enyl)methanol D-hydrogen tartrate

Conditions	Yield
Stage #1: (1S,4R)-methyl 4-aminocyclopent-2-enecarboxylate L-hydrogen tartrate With sodium tetrahydroborate; water; sodium hydroxide at -5 - 0℃; for 4h; Stage #2: D-tartaric acid With sodium hydroxide In methanol at 65℃; for 0.5h; Concentration; Temperature;	88%

2-azabicyclo[2.2.1.]hept-5-en-3-one (49805-30-3) → ((1S,4R)-4-aminocyclopent-2-enyl)methanol D-hydrogen tartrate

Conditions	Yield
Multi-step reaction with 2 steps 1.1: thionyl chloride / 10 - 30 °C / pH 4 - 4.5 1.2: 1 h / 20 - 65 °C 2.1: sodium hydroxide; sodium tetrahydroborate; water / 4 h / -5 - 0 °C 2.2: 0.5 h / 65 °C View Scheme

((1S,4R)-4-aminocyclopent-2-enyl)methanol D-hydrogen tartrate + N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide (171887-03-9) → (1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene (171887-04-0)

Conditions	Yield
Stage #1: ((1S,4R)-4-aminocyclopent-2-enyl)methanol D-hydrogen tartrate With sodium carbonate In isopropyl alcohol at 20℃; for 1h; Stage #2: N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide In isopropyl alcohol Concentration; Solvent; Reflux;	88.2%

Upstream product

• 49805-30-3 2-azabicyclo[2.2.1.]hept-5-en-3-one 
• 147-71-7 D-tartaric acid 
• 419563-22-7 (1S,4R)-methyl 4-aminocyclopent-2-enecarboxylate L-hydrogen tartrate 

Downstream Products

• 171887-04-0 (1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF AMINO ALCOHOL DERIVATIVES OR SALTS THEREOF

The present invention relates to a process for the preparation of amino alcohol derivatives or salts thereof. In particular the present invention relates to process for the preparation of amino alcohol derivatives or salts thereof which may be used as intermediates in the preparation of HIV reverse transcriptase inhibitors, more preferably Carbovir and Abacavir. The present invention more specifically relates to a process for the preparation of (1S,4R)-4-amino-2-cyclopentene-1-methanol of Formula IIIa. The present invention also specifically relates to process for the preparation of Abacavir sulfate of Formula II using compound of Formula IIIa prepared according to the process of the present invention.