1435752-55-8

Basic information

• Product Name: ((1R,3S,5S)-5-acetoxy-3-(2-amino-6-oxo-1H-purin-9(6H)-yl)-2-methylenecyclopentyl)methyl 4-nitrobenzoate
• Synonyms: ((1R,3S,5S)-5-acetoxy-3-(2-amino-6-oxo-1H-purin-9(6H)-yl)-2-methylenecyclopentyl)methyl 4-nitrobenzoate
• CAS NO: 1435752-55-8
• Molecular Weight: 468.426
• Mol File: 1435752-55-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: ((1R,3S,5S)-5-acetoxy-3-(2-amino-6-oxo-1H-purin-9(6H)-yl)-2-methylenecyclopentyl)methyl 4-nitrobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: ((1R,3S,5S)-5-acetoxy-3-(2-amino-6-oxo-1H-purin-9(6H)-yl)-2-methylenecyclopentyl)methyl 4-nitrobenzoate(1435752-55-8)
• EPA Substance Registry System: ((1R,3S,5S)-5-acetoxy-3-(2-amino-6-oxo-1H-purin-9(6H)-yl)-2-methylenecyclopentyl)methyl 4-nitrobenzoate(1435752-55-8)

Safety Data

• Hazardous Substances Data: 1435752-55-8(Hazardous Substances Data)

Upstream product

• 637005-35-7 (3S,5R)-hept-1-en-6-yne-3,5-diol 
• 10310-21-1 2-amino-6-chloropurine 
• 1435752-42-3 ((1R,3R,5S)-5-acetoxy-3-hydroxy-2-methylenecyclopentyl)methyl 4-nitrobenzoate 
• 1435752-36-5 ((1R,3R,5S)-5-acetoxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclopentyl)methyl 4-nitrobenzoate 
• 1383812-06-3 (1S,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)-3-methylenecyclopentyl acetate 
• 1383812-02-9 (1S,3R)-3-(tert-butyldimethylsilyloxy)-1-(oxiran-2-yl)pent-4-ynyl acetate 
• 1383811-98-0 (1S,3R)-3-(tert-butyldimethylsilyloxy)-1-(oxiran-2-yl)pent-4-yn-1-ol 
• 1383811-94-6 (3S,5R)-5-(tert-butyldimethylsilyloxy)hept-1-en-6-yn-3-ol 
• 1383811-90-2 (3S,5R)-5-(tert-butyldimethylsilyloxy)-7-(trimethylsilyl)hept-1-en-6-yn-3-ol 
• 1383811-86-6 (3S,5R)-7-(trimethylsilyl)hept-1-en-6-yne-3,5-diol 
• 10310-21-1 2-Amino-6-chloropurin 

Downstream Products

• 142217-69-4 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one 
• 142217-69-4 entecavir 

Relevant articles and documents

Total synthesis of entecavir

Entecavir (BMS-200475) was synthesized from 4-trimethylsilyl-3-butyn-2-one and acrolein. The key features of its preparation are: (i) a stereoselective boron-aldol reaction to afford the acyclic carbon skeleton of the methylenecylopentane moiety; (ii) its cyclization by a Cp2TiCl- catalyzed intramolecular radical addition of an epoxide to an alkyne; and (iii) the coupling with a purine derivative by a Mitsunobu reaction.

PROCESS FOR PREPARING AN ANTIVIRAL DRUG AND INTERMEDIATES THEREOF

Process for preparing an antiviral drug 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 reactionusing 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.