1294481-81-4

Basic information

• Product Name: (2R,3R,4R,5R)-5-bromo-2-(((4-chlorobenzoyl)oxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl 4-chlorobenzoate
• Synonyms: (2R,3R,4R,5R)-5-bromo-2-(((4-chlorobenzoyl)oxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl 4-chlorobenzoate
• CAS NO: 1294481-81-4
• Molecular Weight: 506.152
• Mol File: 1294481-81-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3R,4R,5R)-5-bromo-2-(((4-chlorobenzoyl)oxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl 4-chlorobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R,5R)-5-bromo-2-(((4-chlorobenzoyl)oxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl 4-chlorobenzoate(1294481-81-4)
• EPA Substance Registry System: (2R,3R,4R,5R)-5-bromo-2-(((4-chlorobenzoyl)oxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl 4-chlorobenzoate(1294481-81-4)

Safety Data

• Hazardous Substances Data: 1294481-81-4(Hazardous Substances Data)

Usage

General Description

The chemical "(2R,3R,4R,5R)-5-bromo-2-(((4-chlorobenzoyl)oxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl 4-chlorobenzoate" is a complex organic compound with a tetrahydrofuran ring structure. It contains bromine, fluorine, chlorine, and methyl groups, as well as a benzoyl ester moiety. The presence of these functional groups suggests that this compound may have pharmaceutical or chemical applications, potentially as a building block or intermediate in the synthesis of other compounds. The specific stereochemistry indicated by the (2R,3R,4R,5R) prefix is also important in determining the compound's properties and potential reactivity in various chemical reactions.

Upstream product

• 1294481-80-3 ((2R,3R,4R,5R)-3-((4-chlorobenzoyl)oxy)-4-fluoro-5-hydroxy-4-methyltetrahydrofuran-2-yl)methyl 4-chlorobenzoate 
• 1294481-79-0 ((2R,3R,4R) 3-(4-chlorobenzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl-4-chlorobenzoate 

Downstream Products

• 1199809-30-7 (2R,3R,4R,5R)-5-(2-amino-6-ethoxy-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-ol 
• 1199809-32-9 PSI-938 
• 1294481-82-5 (2R,3R,4R,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-2-(((4-chlorobenzoyl)oxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl 4-chlorobenzoate 

Relevant articles and documents

Stereoselective synthesis of PSI-352938: A β-D -2′-deoxy- 2′-α-fluoro-2′-β-C-methyl-3′,5′-cyclic phosphate nucleotide prodrug for the treatment of HCV

PSI-352938 is a novel 2′-deoxy-2′-α-fluoro-2′- β-C-methyl 3′,5′-cyclic phosphate nucleotide prodrug currently under investigation for the treatment of hepatitis C virus (HCV) infection. PSI-352938 demonstrated superior characteristics in vitro that include broad genotype coverage, superior resistance profile, and high levels of active triphosphate in vivo in the liver compared to our first and second generation nucleoside inhibitors of this class. Consequently, PSI-352938 was selected for further development and an efficient and scalable synthesis was sought to support clinical development. We report an improved, diastereoselective synthesis of a key 1′-β-nucleoside intermediate 13 via SN2 displacement of 1-α-bromo ribofuranose sugar 16 with the potassium salt of 6-chloro-2-amino purine and an efficient method to prepare cis-Rp cyclic phosphate (PSI-352938) in a highly stereoselective manner without any chromatographic purification. The 1-α-bromo sugar 16 was stereospecifically prepared from the corresponding 1-β-lactol in high yield under mild bromination conditions using CBr4/PPh3 (Appel reaction). The desired cis-Rp 3′,5′-cyclic phosphate construction was accomplished using isopropyl phosphorodichloridate readily obtained from POCl3 and isopropyl alcohol. The base combination of Et 3N/NMI was identified as a key factor for producing PSI-352938 as the major (>95%) diastereomer (cis-Rp) in high yield after the final cyclization step. The current route described in this article was successfully used to produce PSI-352938 on multikilogram scale.