419563-23-8

Usage

Uses

Used in Pharmaceutical Industry:
(1R,4S) Methyl 4-aminocyclopent-2-ene-1-carboxylate D-tartrate is used as an intermediate in the synthesis of ent-Abacavir (A105015) for the development of anti-HIV drugs. Ent-Abacavir is a carbocyclic 2''-deoxyguanosine nucleoside reverse transcriptase inhibitor that helps in treating HIV infection. (1R,4S) Methyl 4-aminocyclopent-2-ene-1-carboxylate D-tartrate is essential in the production of Abacavir, which is metabolized in the liver to its active form, carbovir-triphosphate (CBV-TP), that selectively inhibits HIV reverse transcriptase by incorporating into viral DNA. This makes it a vital component in the fight against HIV and AIDS.

Upstream product

• 67-56-1 methanol 
• 147-71-7 D-tartaric acid 
• 49805-30-3 racemic 2-azabicyclo[2.2.1]hept-5-en-3-one 
• 49805-30-3 2-azabicyclo[2.2.1.]hept-5-en-3-one 

Downstream Products

• 251326-99-5 (1R,4S)-N-tert-butoxycarbonyl-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester 
• 153011-43-9 (1S,cis)-tert-butyl N-[4-(hydroxymethyl)-2-cyclopenten-1-yl]carbamate 
• 134003-04-6 (1R,4S)-4-aminocyclopenten-2-ene-1-carboxylic acid 

Relevant academic research and scientific papers

Chemical preparation method of 2-azabicyclo [2.2.1] hept-5-ene-3-one with optical activity

The invention discloses a chemical preparation method of 2-azabicyclo [2.2.1] hept-5-ene-3-one with optical activity. The chemical preparation method comprises the following steps: racemic 2-azabicyclo [2.2.1] hept-5-ene-3-one which is easily available on the market is used as a raw material and is subjected to chemical resolution to obtain (+/-) 4-aminocyclopent-2-ene-1-carboxylic acid methyl ester with optical activity, (+/-) 4-aminocyclopent-2-ene-1-carboxylic acid is prepared by hydrolysis, and the (+/-) 4-aminocyclopent-2-ene-1-carboxylic acid is subjected to intramolecular condensation to obtain the 2-azabicyclo [2.2.1] hept-5-ene-3-one with optical activity. The method has the advantages that the use of an enzyme fermentation method is avoided, the repeatability is good, and the yield is high.

Optical pure amino alcohol hydrochloride preparation method

The invention relates to a preparation method for optically pure aminoalcohol hydrochloride. The optically pure aminoalcohol hydrochloride is any one selected from optically pure aminoalcohol hydrochloride 1 and optically pure aminoalcohol hydrochloride 2 and is prepared by subjecting a compound 4 to an esterification ring-opening reaction, an amino protection reaction, an ester reduction reaction and a deprotection salt forming reaction. The optically pure aminoalcohol hydrochloride 1 or optically pure aminoalcohol hydrochloride 2 prepared in the invention can be directly used for synthesis of abacavir and carbovir. The preparation method provided by the invention has the advantages of high product optical purity, stable product quality, high product yield, a small amount of environmental pollution, low production cost, easy industrialization, etc.

Process for preparing (-)-(1S, 4R) N-protected 4-amino-2-cyclopentene-1-carboxylate esters

The invention relates to a process for preparing (?)-(1S,4R) N protected 4-amino-2-cylcopentene-1-carboxylate esters represented by the formula (I) wherein R1 and R2 are as described within the specification.