Synthesis of 9-(2,3-dideoxy-2,3-difluoro-β-D-arabinofuranosyl)adenine

Nucleosides, Nucleotides and Nucleic Acids

Volumn 26, Issue 10-12, 2007, Pages 1387-1389

  Sivets, Grigorii G ^a   Kalinichenko, Elena N ^a   Mikhailopulo, Igor A ^a,b  

^a INSTITUTE OF BIOORGANIC CHEMISTRY   (Belarus)

^b UNIVERSITY OF EASTERN FINLAND   (Finland)

Author keywords

Convergent synthesis; Dideoxydifluoro nucleosides; Purine

Indexed keywords

9 (2,3 DIDEOXY 2,3 DIFLUORO BETA DEXTRO ARABINOFURANOSYL)ADENINE; ADENINE DERIVATIVE; ARABINOFURANOSIDASE; METHYL 5 O BENZYL 2 DEOXY 2 FLUORO ALPHA D ARABINOFURANOSIDE; UNCLASSIFIED DRUG;

ARTICLE; POLYMERIZATION; SYNTHESIS;

ADENINE; DIDEOXYADENOSINE;

EID: 37049013501     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770701534063     Document Type: Article

References (9)

1. Pankiewicz, K.W. Fluorinated nucleosides. Carbohydr. Res. 2000, 327, 87-105.
2. Sivets, G.G.; Kalinichenko, E.N.; Mikhailopulo, I.A. Synthesis of C2′-β-fluoro-substituted adenine nucleosides via pivaloyl derivatives of adenosine and 3′-deoxyadenosine. Letters Org. Chem. 2006, 5, 402-408.
3. Wright, J.A.; Taylor, N.F.; Fox, J.J. Nucleosides. LX. Fluorocarbohydrates. XXII. Synthesis of 2-deoxy-2-fluoro-D-arabinose and 9-(2-deoxy-2-fluoro-α- and β-arabinofuranosyl)adenines. J. Org. Chem. 1969, 34, 2632-2636.
4. Mikhailopulo, I.A.; Sivets, G.G.; Poopeiko, N.E.; Khripach, N.B. Oxidation-reduction sequence for the synthesis of peracylated fluorodeoxy pentofuranosides. Carbohydr. Res. 1995, 278, 71-89.
5. Mikhailopulo, I.A.; Pricota, T.I.; Sivets, G.G.; Altona, C. 2′-Chloro-2′,3′-dideoxy-3′-fluoro-D- ribofuranosides: Synthesis, stereospecificity, some chemical transformations, and conformational analysis. J. Org. Chem. 2003, 68, 5897-5908.
6. Gillard, J.W.; Israel, M. Trimethylsilyl bromide as a mild, stereoselective anomeric brominating agent. Tetrahedron Lett. 1981, 22, 513-516.
7. Jin, F.; Wang, D.; Confalone, P.N.; Pierce, M.E.; Wang, Z.; Xu, G.; Choudhury, A.; Nguyen, D. (2R,3S,5S)-2-Acetoxy-3-fluoro-5- (p-toluoyloxymethyl)tetrahydrofuran: A key intermediate for the practical synthesis of 9-(2,3-dideoxy-2-fluoro-β-D-threo- pentofuranofuranosyl)adenine (FddA). Tetrahedron Lett. 2001, 42, 4787-4789.
8. Martin, J.A.; Busnell, D.J.; Duncan, I.B.; Dunsdon, S.J.; Hall, M.J.; Machin, P.J.; Merret, J.H.; Parkes, K.E.B.; Roberts, N.A.; Thomas, G.J.; Galpin, S.A.; Kinchington, D. Synthesis and antiviral activity of monofluoro and difluoro analogues of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1). J. Med. Chem. 1990, 33, 2137-2145.
9. 5′,3′F = 1.15; H-5″).