197452-31-6

Basic information

• Product Name: 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-L-erythro-pentofuranos-1-yl)-5-fluorocytosine
• CAS NO: 197452-31-6
• Molecular Weight: 489.408
• Mol File: 197452-31-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-L-erythro-pentofuranos-1-yl)-5-fluorocytosine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-L-erythro-pentofuranos-1-yl)-5-fluorocytosine(197452-31-6)
• EPA Substance Registry System: 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-L-erythro-pentofuranos-1-yl)-5-fluorocytosine(197452-31-6)

Safety Data

• Hazardous Substances Data: 197452-31-6(Hazardous Substances Data)

Upstream product

• 2022-85-7 Flucytosine 
• 197452-17-8 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-(methylsulfonyl)-L-erythro-pentofuranose 
• 166376-98-3 (R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-difluoro-3-hydroxy-propionic acid ethyl ester 
• 197452-15-6 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-L-erythro-pentono-γ-lactone 
• 143157-25-9 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-L-erythro-pentofuranose 
• 166275-25-8 (4S,5S)-3,3-Difluoro-4-hydroxy-5-hydroxymethyl-dihydro-furan-2-one 
• 98-88-4 benzoyl chloride 

Relevant articles and documents

Structure-activity relationships of 2'-deoxy-2',2'-difluoro-L-erythro- pentofuranosyl nucleosides

Following the recent discoveries that some L-nucleosides are more or equal potent than their D-counterparts, we synthesized 2'-deoxy-2',2'- difluoro-L-erythro-pentofuranosyl nucleosides as potential antiviral agents. The target compounds were synthesized via the key intermediates 7a or 7b from L-gulono γ-lactone. Compound 2 was oxidatively cleaved and coupled with ethyl bromodifluoroacetate in the presence of activated zinc under Reformatsky conditions to obtain a diastereomeric mixture of 4(R) and 4(S), in a 4:1 ratio. The major 4(R) isomer was cyclized and treated appropriately to obtain the mesylate 8a or 8b, which was condensed with various silyl- protected pyrimidines. Condensation of the alcohol 7a or 7b with 6- chloropurine under Mitsunobu conditions afforded the 6-chloropurine analogs 53a or 53b and 54a or 54b. Further treatment of the compounds 53a, 54a and 53b, 54b afforded the inosine and adenine derivatives 57-60, respectively. The condensation of 2-amino-6-chloropurine with compound 8a and subsequent treatment with 2-mercaptoethanol/sodium methoxide afforded the guanine analogs 63 and 64. All of the synthesized nucleosides 31-52, 57-60, 63, and 64 were evaluated for antiviral activity and for cellular toxicity. Adenine derivative 57 showed a moderate activity against HIV-1 in PBM cells (3.4 μM). None of the other compounds showed any significant activities against HIV-1, HBV, HSV-1, HSV-2, and toxicity in Veto, CEM, and PBM cell lines up to 100 μM. The X-ray structure of the 5-iodocytosine analog showed a 2'- exo/3'-endo conformation for the carbohydrate moiety, which is different from those of the biologically active compounds (-)-FTC and L-FMAU.