Synthesis of (2,3,4,6-tetra-O-acetyl-α-D-glycopyranosyl) thiophene derivatives as new C-nucleoside analogues

Journal of Carbohydrate Chemistry

Volumn 20, Issue 7-8, 2001, Pages 681-687

  Garcia, Ivette ^a,b   Feist, Holger ^b   Cao, Roberto ^a   Michalik, Manfred ^b   Peseke, Klaus ^b  

^a UNIVERSITY OF HAVANA   (Cuba)

^b UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

STAPHYLOCOCCUS PHAGE 3A;

EID: 0035648908     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1081/CAR-100108282     Document Type: Article

References (19)

1. th birthday.
2. Pinto, I. L.; Jarvest, R. L.; Serafinowska, H. T. The Synthesis of 5-Alkoxy and 5-Amino Substituted Thiophenes. Tetrahedron Lett. 2000, 41, 1597-1600.
3. Rosowsky, A.; Mota, C. E.; Wright, J. E.; Freisheim, J. H.; Heusner, J. J.; McCormack, J. J.; Queener, S. F. 2,4-Diaminothieno[2,3-d]pyrimidine Analogues of Trimetrexate and Piritrexim as Potential Inhibitors of Pneumocystis carinii and Toxoplasma gondii Dihydrofolate Reductase. J. Med. Chem. 1993, 36, 3103-3112.
4. Huybrechts, L.; Buffel, D.; Freyne, E.; Hoornaert, G. The Synthesis of 5-Carboxamido-4-hydroxy-3(β-D-ribofuranosyl)-thiophene Derivatives, Analogues of Pyrazofurin. Tetrahedron, 1984, 40, 2479-2485.
5. Dave, C. G.; Shah, P. R.; Shah, A. B.; Dave, K. C.; Patel, V. J. Synthesis and Biological Activity of Pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidines. J. Indian Chem. Soc. 1989, 66, 48-50.
6. Levy, D. E.; Tang, C. The Chemistry of C-Glycosides, Pergamon Press, Oxford, 1995, 10-11.
7. Buchanan, J. G.; Wightman, R. H. The C-Nucleoside Antibiotics. Prog. Chem. Org. Nat. Prod. 1984, 44, 243-299.
8. Humber, D. C.; Mulholland, K. R.; Stoodley, R. J. C-Nucleosides. Part 1.Preparation of Tiazofurin and N-Substituted Tiazofurins from Benzyl(2′,3′,5′-Tri-O-benzoyl-β-D-ribofuranosyl)penicilli nate. J. Chem. Soc., Perkin Trans, 1, 1990, 283-292.
9. Rudloff, I.; Peseke, K.; Reinke, H. Syntheses of Acyclo-C-nucleosides by Ring Transformation of 2(3)-Formyl-glycals. J. Prakt. Chem. 1998, 340, 334-340.
10. Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. Synthesis of Carbonlinked Glycopeptides through Catalytic Asymmetric Hydrogenation. J. Am. Chem. Soc. 1997, 119, 9897-9898.
11. Peseke, K.; Feist, H.; Hanefeld, W.; Kopf, J.; Schulz, H. BrancheD-chain Sugars as Push-pull Butadienes. J. Carbohydr. Chem. 1995, 14, 317-325.
12. Texier-Boullet, F.; Focaud, A. Knoevenagel Condensation Catalyzed by Aluminium Oxide. Tetrahedron Lett. 1982, 23, 4927-4728.
13. Elassar, A.-Z. A.; Elkholy, Y. M.; Elnagdi, M. H. Chemistry of Crotononitrile. J. Prakt. Chem. 1998, 340, 491-505 (1998).
14. Gewald, K.; Kleinert, M.; Thiele, B.; Hentschel, M. Zur basenkatalysierten Reaktion von methylenaktiven Nitrilen mit Schwefel. J. Prakt. Chem. 1972, 314, 303-314.
15. Unverferth, K. Wirkstoffe durch GewalD-Reaktionen. Pharmazie 1990, 45, 545-548 (1990).
16. Gómez, M.; Quincoces, J.; Peseke, K.; Michalik, M.; Reinke, H. J. Synthesis of anellated Pyranose Derivatives on the Basis of Levoglucosenone. J. Carbohydr. Chem. 1999, 18, 851-865.
17. Taylor, E. C.; Berger, J. Heterocyclic Syntheses from o-Aminonitriles. XXIX. A New Synthesis of 5-Substituted Pyrimidines. J. Org. Chem. 1967, 32, 2376-2378.
18. Horton D.; Miyake, T. Steroselective Syntheses of C-(D-Glucopyranosyl)alkenes. Carbohydr. Res. 1988, 184, 221-229.
19. Tronchet, J. M. J.; Zsély, M.; Geoffroy, M. Spin-labelled Glycolipid Analogues: D-Glucose Series. Carbohydr. Res. 1995, 275, 245-258.