Synthesis of a novel aldehyde: 4-O-methyl-5-formylmethyl-2′-deoxyuridine

Nucleosides, Nucleotides and Nucleic Acids

Volumn 22, Issue 1, 2003, Pages 71-84

  Yu, Chung Shan ^a,b   Oberdorfer, Franz ^a,c  

^a GERMAN CANCER RESEARCH CENTER DKFZ   (Germany)

^b INSTITUTE OF CHEMISTRY   (Taiwan)

^c NONE   (Germany)

Author keywords

Aldehyde; Deoxyuridine; Dithioacetals; Gem difluoro; Reductive tritualation

Indexed keywords

1 (3,5 DI O 4 TOLUOYL 2 DEOXY BETA DEXTRO ERYTHRO PENTAFURANOSYL) 5 [(1,3 DITHIAN 2 YL)METHYL] 4 METHOXYPYRIMIDIN 2 ONE; 4 O METHYL 5 FORMYLMETHYL 2' DEOXYURIDINE; ALDEHYDE DERIVATIVE; DEOXYCYTIDINE; DEOXYURIDINE DERIVATIVE; GAMMA BUTYROLACTONE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THIN LAYER CHROMATOGRAPHY;

ALDEHYDES; DEOXYURIDINE; PRODRUGS; THYMIDINE;

EID: 0037241324     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1081/NCN-120018624     Document Type: Article

References (19)

1. Springer, C.J.; Niculescu-Duvaz, I. Molecular imaging and gene therapy. Clin. Invest. 2000, 105, 1161.
2. (a) Nichol, C.; Kim, E.E. Imaging transgene expression with radionuclide imaging technologies. J. Nucl. Med. 2001, 42, 1368.
3. (b) Gambhir, S.S.; Herschman, H.R.; Cherry, S.R.; Barrio, J.R.; Satyamurthy, N.; Toyokuni, T.; Phelps, M.E.; Larson, S.M.; Balatoni, J.; Finn, R.; Sadelain, M.; Tjuvajev, J.; Blasberg, R. Non-invasive radiotracer imaging as a tool for drug development. Neoplasia 2000, 2, 118.
4. (c) Gibson, R.E.; Burns, H.D.; Hamill, T.G.; Eng, W.S.; Francis, B.E.; Ryan, C. Assays for noninvasive imaging of reporter gene expression - Noninvasive radiotracer imaging as a tool for drug development. Curr. Pharm. Design 2000, 6, 973.
5. (d) Gambhir, S.S.; Bario, J.R.; Herschman, H.R.; Phelps, M.E. Assays for noninvasive imaging of reporter gene expression. Nucl. Med. Biol. 1999, 26, 481.
6. Yu, C.S.; Oberdorfer, F. Synthesis of 4-O-methyl-protected 5-(2-hydroxyethyl)-2′-deoxyuridine derivatives and their nucleophilic fluorination to 5-(2-Fluoroethyl)-2′-deoxyuridine. Synthesis 1999, 2057.
7. (a) Yu, C.S.; Oberdorfer, F. Synthesis of (E)-5-[2-(tri-n-butylstannyl)vinyl] substituted 2′-deoxyuridine derivatives for use in halogenation and radiohalogenation reactions. Synlett 2000, 86.
8. (b) Yu, C.S.; Eisenbarth, J.; Runz, A.; Weber, K.; Zeisler, S.; Oberdorfer, F. Syntheses of 5-(2-radiohaloethyl)- and 5-(2-radiohalovinyl)-2′-deoxyuridines: Novel types radiotracer for monitoring cancer gene therapy with PET. J. Label. Compd. Radiopharm. 2003, 46, 1-19.
9. For reviews, see: (a) Kitazume, T.; Yamazaki, T. Chambers R.D., Ed.; Organofluorine chemistry: techniques and synthons. Topics in Current Chemistry; Springer Verlag: 1997; Vol. 193, 91-130.
10. (b) Percy, J.M. Building block approaches to aliphatic organofluorine compounds. Top. Curr. Chem. 1997, 193, 131.
11. Kuroboshi, M.; Kanie, K.; Hiyama, T. Oxidative desulfurization-fluorination: A facile entry to a wide variety of organofluorine compounds leading to novel liquid-crystalline materials. Adv. Synth. Catal. 2001, 343, 235.
12. Constantinou, M.; Aigbirhio, F.I.; Smith, R.G.; Ramsden, C.A.; Pike, V.W. Xenon difluoride exchanges fluoride under mild conditions: A simple preparation of [F-18]Xenon difluoride for PET and mechanistic studies. J. Am. Chem. Soc. 2001, 123, 1780.
13. Fissekis, J.D.; Sweet, F. The chemistry of some 5-(2-hydroxyalkyl)uracil derivatives and a synthesis of 5-vinyluracil. J. Org. Chem. 1973, 38, 264-269. Though 5-(2-hyroxyethyl)uracil 12 has been reported as early as in 1973 by Fissekis et al., they failed in oxidation of the primary hydroxyl to obtain 5-formylmethyl uracil 10.
14. Bergstrom, D.E.; Agosta, W.C. The photosensitized cycloaddition of uracil to vinylene carbonate: A route to 5-(formylmethyl)uracil and (+)-5-(4′,5′-dihydroxypentyl)uracil. Tetrahedron Lett. 1974, 13, 1087.
15. 80Br-Labelled Nucleoside Analogues. Useful Tools for Monitoring Gene Therapy." University of Heidelberg, Apr. 1999.
16. (a) Tidwell, T.T. In organic reactions. Paquette L.A. Ed.; Oxidation of Alcohols to Carbonyl Compounds via Alkoxysulfonium Ylides: The Moffatt, Swern and Related Oxidations John Wiley & Sons, 1990, Vol. 39, pp 304-307.
17. (b) Brossmer, R.; Ziegler, D. Zur darstellung heterocyclischer aldehyde. Tetrahedron Lett. 1966, 5253.
18. Griengl, H.; Wanek, E.; Schwarz, W.; Streicher, W.; Rosenwirth, B.; De Clercq, E. 2′-fluorinated arabinonucleosides of 5-(2-haloalkyl)uracil: synthesis and antiviral activity. J. Med. Chem. 1987, 30, 1199.
19. Wong, J.L.; Fuchs, D.S. Competitive isomerization and dealkylation of 2,4-dialkoxy pyrimidines in aqueous and nonaqueous media. J. Org. Chem. 1970, 35, 3786.