96245-84-0

Upstream product

• 3601-90-9 5-chloro-2-(((4-chlorobenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-chlorobenzoate 
• 79387-69-2 5-iodo-2(1H)-pyrimidinone 
• 38953-72-9 5-iodo-2,4-bis-O-trimethylsilyluracil 
• 21740-23-8 3,5-O-bis(4-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl chloride 
• 88350-65-6 5-iodo-2-((trimethylsilyl)oxy)pyrimidine 

Downstream Products

• 93265-81-7 1-(2-Deoxy-beta-D-ribofuranosyl)-5-(iodo)-2-pyrimidinone 

Relevant academic research and scientific papers

Preparation method of 1-(2-deoxy-beta-D-ribofuranose)-5-iodo-2-pyrimidone

The invention relates to 1-(2-deoxidized-beta-D-ribofuranose)-5-iodo-2-pyrimidone, and particularly relates to a preparation method of 1-(2-deoxidized-beta-D-ribofuranose)-5-iodo-2-pyrimidone. The preparation method comprises the following steps of performing a reaction on 2-hydroxypyrimidine hydrochloride and a glacial acetic acid/iodine monochloride solution so as to generate 5-iodo-2-pyrimidone; performing a reaction on the 5-iodo-2-pyrimidone and 1-chloro-3,5-di(4-chlorbenzoyl)-2-deoxy-D-ribose so as to generate 1-[(3,5-di(4-chlorbenzoyl)-2-deoxy-beta-D-erythro-pentofuranose]-5-iodo-2-pyrimidone; and finally generating a target product by using the 1-[(3,5-di(4-chlorbenzoyl)-2-deoxy-beta-D-erythro-pentofuranose]-5-iodo-2-pyrimidone. All intermediates are stable, the yield is high, andthe method is suitable for industrial production.

Improved stereoselective synthesis of the β-anomer of 1-[3,5-bis-0-(p-chlorobenzoyl)-2-deoxy-D-ribofuranosyl]-5-iodo-2-pyrimidinone

The lack of stereochemical control has been a major hurdle in synthesizing β-nucleosides in large scale. This paper reports a study of the effects of different catalysts used in the synthesis of β-nucleosides. The effects of time and temperature on α- and β-anomers are illustrated in this paper. The yield and selectivity of the β-nucleoside have been improved vastly at temperatures between -30 and -40 °C and by using SnCl4 as the catalyst.

Synthesis and Biological Activities of 2-Pyrimidinone Nucleosides. 2. 5-Halo-2-pyrimidinone 2'-Deoxyribonucleosides

1-(2-Deoxy-β-D-ribofuranosyl)-5-bromo-2-pyrimidinone (BrPdR) and 1-(2-deoxy-β-D-ribofuranosyl)-5-iodo-2-pyrimidinone (IPdR) have been synthesized by condensation of the appropriate silylated bases 2a and 2b, respectively, with 3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl chloride (8) in 1,2-dichloroethane, in the presence of SnCl4, followed by separation of the anomeric blocked nucleosides via column chromatography and subsequent deprotection with methanolic ammonia.Both BrPdR and IPdR exhibited significant antiherpes activities against various strains of HSV-1 and HSV-2, the latter compound (IPdR) showing the higher activity as well as the stronger binding to the virus-specific thimidine kinase.