188399-46-4

Basic information

• Product Name: 6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(1R,3S,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-
• Synonyms: 6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(1R,3S,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-;2-Amino-1,9-dihydro-9-[(1R,3S,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one;[1R-(1α,3α,4β)]-2-AMino-1,9-dihydro-9-[4-hydroxy-3-(hydroxyMethyl)-2-Methylenecyclopentyl]-6H-purin-6-one;ent-Entecavir;2-Amino-9-((1R,3S,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl)-1H-purin-6(9H)-one;Entecavir Enantiomer (1R,3S,4R);2-amino-9-((1R,3S,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl)-1,9-dihydro-6H-purin-6-one;(1R,3S,4R)-Entecavir
• CAS NO: 188399-46-4
• Molecular Formula: C12H15N5O3
• Molecular Weight: 277
• Mol File: 188399-46-4.mol

Chemical Properties

• Appearance: /
• Density: 1.81
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9?+-.0.20(Predicted)
• CAS DataBase Reference: 6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(1R,3S,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(1R,3S,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-(188399-46-4)
• EPA Substance Registry System: 6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(1R,3S,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-(188399-46-4)

Safety Data

• Hazardous Substances Data: 188399-46-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(1R,3S,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]is used as an enantiomeric impurity of the antiviral drug Entecavir (E558900). It plays a crucial role in the development and manufacturing process of Entecavir, ensuring the purity and efficacy of the final drug product. 6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(1R,3S,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-'s presence in the pharmaceutical industry is essential for maintaining the quality and safety of antiviral medications.
Used in Chemical Research:
6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(1R,3S,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]is also used in chemical research for its unique molecular structure and properties. Researchers can study its chemical behavior, interactions with other compounds, and potential applications in various fields. 6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(1R,3S,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]can contribute to the advancement of knowledge in organic chemistry and the development of new pharmaceuticals and materials.

Upstream product

• 1383811-98-0 (1S,3R)-3-(tert-butyldimethylsilyloxy)-1-(oxiran-2-yl)pent-4-yn-1-ol 
• 1383811-86-6 (3S,5R)-7-(trimethylsilyl)hept-1-en-6-yne-3,5-diol 
• 1383811-90-2 (3S,5R)-5-(tert-butyldimethylsilyloxy)-7-(trimethylsilyl)hept-1-en-6-yn-3-ol 
• 1383811-94-6 (3S,5R)-5-(tert-butyldimethylsilyloxy)hept-1-en-6-yn-3-ol 
• 1383812-02-9 (1S,3R)-3-(tert-butyldimethylsilyloxy)-1-(oxiran-2-yl)pent-4-ynyl acetate 
• 1383812-06-3 (1S,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)-3-methylenecyclopentyl acetate 
• 701278-65-1 (1S,2R,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)-3-methylenecyclopentanol 
• 1383812-22-3 ((1 R,3S,5S)-5-acetoxy-3-(2-amino-6-chloro-9H-purin-9-yl)-2-methylenecyclopentyl)methyl acetate 
• 1383812-10-9 ((1R,3R,5S)-5-acetoxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclopentyl)methyl acetate 
• 1435752-36-5 ((1R,3R,5S)-5-acetoxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclopentyl)methyl 4-nitrobenzoate 
• 1435752-42-3 ((1R,3R,5S)-5-acetoxy-3-hydroxy-2-methylenecyclopentyl)methyl 4-nitrobenzoate 
• 1435752-48-9 ((1R,3S,5S)-5-acetoxy-3-(2-amino-6-chloro-9H-purin-9-yl)-2-methylenecyclopentyl)methyl 4-nitrobenzoate 
• 10310-21-1 2-Amino-6-chloropurin 
• 1435752-55-8 ((1R,3S,5S)-5-acetoxy-3-(2-amino-6-oxo-1H-purin-9(6H)-yl)-2-methylenecyclopentyl)methyl 4-nitrobenzoate 

Relevant articles and documents

Process for preparing entecavir and intermediates thereof

It comprises the preparation of entecavir of formula (I), or a pharmaceutically acceptable salt thereof, or a hydrate thereof by submitting a compound of formula (III) where X is an halogen selected from Cl, Br, and I, first to a hydrolysis reaction using formic acid and then to a deprotection reaction, and isolating the entecavir either as free base or as a pharmaceutically acceptable salt. It also comprises intermediates which intervene in this preparation process.

Preparation process of an antiviral drug and intermediates thereof

Preparation process of an antiviral drug and intermediates thereof It comprises a preparation process of entecavir comprising: submitting a (1S,3R)-3-(tert-butyldimethylsilyloxy)-1-(oxiran-2-yl)pent-4-yn-1-ol (VIII) to a double esterification and to a radicalary cyclization, yielding a compound of formula (V), where either a compound of formula (VIII) is submitted to a first esterification reaction, then to a catalytic radicalary cyclization using titanocene dichloride as catalyst in the presence of Mn/2,4,6-collidine HCl or Zn/2,4,6-collidine/trimethylsilyl chloride, and finally to a second esterification reaction or, alternatively, the compound of formula (VIII) is submitted first to a catalytic radicalary cyclization, and then to an esterification reaction. Entecavir can be obtained by submitting compound (V) to a desilylation reaction to remove the TBS group and then to a Mitsunobu coupling with 2-amino-6-chloroguanine, followed by hydrolysis. It also relates to some new intermediates of the process.