1013918-32-5

Basic information

• Product Name: C₂₄H₁₇FN₁₀O₅
• Synonyms: C₂₄H₁₇FN₁₀O₅
• CAS NO: 1013918-32-5
• Molecular Weight: 544.461
• Mol File: 1013918-32-5.mol

Chemical Properties

• CAS DataBase Reference: C₂₄H₁₇FN₁₀O₅(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₄H₁₇FN₁₀O₅(1013918-32-5)
• EPA Substance Registry System: C₂₄H₁₇FN₁₀O₅(1013918-32-5)

Safety Data

• Hazardous Substances Data: 1013918-32-5(Hazardous Substances Data)

Upstream product

• 5451-40-1 2,6 dichloropurine 
• 97614-43-2 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose 
• 329187-80-6 ((2R,3R,4S,5R)-3-(benzoyloxy)-5-(2,6-dichloro-9H-purin-9-yl)-4-fluorotetrahydrofuran-2-yl)methyl benzoate 
• 75788-35-1 9-Trimethylsilyl-2,6-dichlorpurin 

Downstream Products

• 103884-97-5 9-(2’-deoxy-2’-fluoro-β-D-arabinofuranos-1’-yl)-2-amino-6-aminopurine 
• 103884-98-6 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-guanine 

Relevant articles and documents

Synthesis and anti-HIV activity of 2′-fluorine modified nucleoside phosphonates: Analogs of GS-9148

Modified purine analogs of GS-9148 [5-(6-amino-purin-9-yl)-4-fluoro-2,5-dihydro-furan-2-yloxymethyl]-phosphonic acid (2′-Fd4AP) were synthesized and their anti-HIV potency evaluated. The antiviral activity of guanosine analog (2′-Fd4GP) was comparable that of to 2′-Fd4AP in MT-2 cells, but selectivity was reduced.

Oligonucleotides containing 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-adenine and -guanine: Synthesis, hybridization and antisense properties

Synthesis of 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-adenine (7, ara-A2′F) and -guanine (12, ara-G2′F) was accomplished via the condensation of 2,6-dichloropurine (1) with 2-deoxy-2-fluoro-1,3,5-tri-O-benzoyl-α-D-arabinofuranose (2) as a key chemical step. Condensation of silylated N6-benzoyladenine (6) with 2 gave, after deblocking and chromatographic separation, ara-A2′F (7) (14%), it's α-anomer 8 (14%) and N7-α-isomer 9 (25%). The PSEUROT analysis of N9-β-D-arabinosides 7 and 12 manifested slight preference for the S rotamer (64%) for the former, and an equal population of the N and S rotamers for the latter. The arabinosides 7 and 12 were used for the preparation of the respective phosphoamidite building blocks 13 and 14 for automated oligonucleotide synthesis. Four 15-mer oligonucleotides (ONs) complementary to the initiation codon region of firefly luciferase mRNA were prepared: unmodified 2′-deoxy-ON (AS 1) and containing (i) ara-A2′F instead of the only A (AS2), (ii) ara-G2′F vs. 3-G from the 5′-terminus (AS3), and (iii) both arabinosides at the same positions (AS4). All these ONs display practically the same (i) affinity to both complementary DNA and RNA, and (ii) ability to inhibit a luciferase gene expression in a cell-free transcription-translation system.