896109-84-5

Basic information

• Product Name: 1-(2'-deoxy-2',2'-difluoro-5-benzoyl-3-(4-phenyl)benzoyl-β-D-arabinofuranosyl)-4-aminopyrimidine-2-one
• Synonyms: 1-(2'-deoxy-2',2'-difluoro-5-benzoyl-3-(4-phenyl)benzoyl-β-D-arabinofuranosyl)-4-aminopyrimidine-2-one
• CAS NO: 896109-84-5
• Molecular Weight: 547.515
• Mol File: 896109-84-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1-(2'-deoxy-2',2'-difluoro-5-benzoyl-3-(4-phenyl)benzoyl-β-D-arabinofuranosyl)-4-aminopyrimidine-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2'-deoxy-2',2'-difluoro-5-benzoyl-3-(4-phenyl)benzoyl-β-D-arabinofuranosyl)-4-aminopyrimidine-2-one(896109-84-5)
• EPA Substance Registry System: 1-(2'-deoxy-2',2'-difluoro-5-benzoyl-3-(4-phenyl)benzoyl-β-D-arabinofuranosyl)-4-aminopyrimidine-2-one(896109-84-5)

Safety Data

• Hazardous Substances Data: 896109-84-5(Hazardous Substances Data)

Upstream product

• 874633-78-0 5-O-benzoyl-2-deoxy-2,2-difluoro-3-O-(p-phenylbenzoyl)-α-D-ribofuranosyl bromide 
• 18037-10-0 2,4-O,N-bis(trimethylsilyl)cytosine 
• 71-30-7 Cytosine 
• 65-46-3 CYTIDINE 

Downstream Products

• 95058-81-4 gemcitabine 

Relevant articles and documents

An efficient large-scale synthesis of gemcitabine employing a crystalline 2, 2-difluoro-α-ribofuranosyl bromide

An efficient large-scale synthesis of gemcitabine was achieved without chromatography or fractional crystallization. The key steps include stereospecific conversion of a novel β-ribofuranosyl phosphate into a highly crystalline a-ribofuranosyl bromide and coupling of the α-ribofuranosyl bromide and trime- thylsilyl cytosine to produce a β-nucleoside. p-Phenylbenzoyl group was introduced for the protection of one of hydroxy groups in order to enhance the crystallinity of intermediates. Continuous removal of trimethylsilyl bromide, generated during the coupling reaction, by distillation from the reaction medium substantially enhanced the β-selectivity of the crucial coupling reaction.

A NOVEL AND HIGHLY STEREOSELECTIVE PROCESS FOR PREPARING GEMCITABINE AND INTERMEDIATES THEREOF

The present invention provides a novel and highly stereoselective process for preparing gemcitabine, which is suitable for industrial production, wherein, it includes the following reactions. Additionally, the invention discloses the key intermediates. The definition for the groups of G1, G2, G3, G4, and G5 are described in the specification.

METHOD FOR THE PREPARATION OF 2#-DEOXY-2#,2#-DIFLUOROCYTIDINE

This invention relates to an improved method for stereoselectively preparing 2′-deoxy-2′,2′-difluorocytidine of formula (I), which comprises the steps of reacting a 1-halo ribofuranose compound of formula (III) with a nucleobase of formula (IV) in a solvent to obtain a nucleoside of formula (II) with removing the silyl halide of formula (V) produced during the reaction; and deprotecting the nucleoside of formula (II) to obtain 2′-deoxy-2′,2′-difluorocytidine of formula (I).