A diastereoselective synthesis of 5'-substituted-uridine derivatives

Journal of Organic Chemistry

Volumn 79, Issue 16, 2014, Pages 7758-7765

  Fer, Mickaël J ^a   Doan, Pierre ^a   Prangé, Thierry ^b   Calvet Vitale, Sandrine ^a   Gravier Pelletier, Christine ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

REGIOSELECTIVITY; STEREOSELECTIVITY;

DIASTEREOSELECTIVE EPOXIDATION; DIASTEREOSELECTIVE SYNTHESIS; REGIO-SELECTIVE; STRAIGHTFORWARD STRATEGY;

X RAY DIFFRACTION ANALYSIS;

5' (BUTYLAMINOMETHYL) 2',3' DI O (TERT BUTYLDIMETHYLSILYL)URIDINE; 5' C (4 BROMO PHENYLOXYMETHYL) 2',3' DI O (TERT BUTYLDIMETHYLSILYL)URIDINE; 5' C (AZIDOMETHYL) 2',3' DI O (TERT BUTYLDIMETHYLSILYL)URIDINE; 5' C (BENZYLOXYMETHYL) 2',3' DI O (TERT BUTYLDIMETHYLSILYL)URIDINE; 5' C (BROMOMETHYL) 2',3' DI O (TERT BUTYLDIMETHYLSILYL)URIDINE; 5' C (CYANOMETHYL) 2',3' DI O (TERT BUTYLDIMETHYLSILYL)URIDINE; 5' C (METHYL LEVO ALANINATE N METHYL) 2',3' DI O (TERT BUTYLDIMETHYLSILYL)URIDINE; 5' C (METHYL SERINATE N METHYL) 2',3' DI O (TERT BUTYLDIMETHYLSILYL)URIDINE; 5' C (MORPHOLINO N METHYL) 2',3' DI O (TERT BUTYLDIMETHYLSILYL)URIDINE; 5' C (N' BENZYL N METHYL) 2',3' DI O (TERT BUTYLDIMETHYLSILYL)URIDINE; 5' C (N' BUTYL N METHYL) 2',3' DI O (TERT BUTYLDIMETHYLSILYL)URIDINE; 5' C (N' PHENYL N METHYL) 2',3' DI O (TERT BUTYLDIMETHYLSILYL)URIDINE; 5' C (PHENYLOXYMETHYL) 2',3' DI O (TERT BUTYLDIMETHYLSILYL)URIDINE; 5' C (PHENYLTHIOMETHYL) 2',3' DI O (TERT BUTYLDIMETHYLSILYL)URIDINE; 5' C (TRIMETHYLSILYLACETYLENYLMETHYL) 2',3' DI O (TERT BUTYLDIMETHYLSILYL)URIDINE; 5' METHYLIDENEURIDINE; UNCLASSIFIED DRUG; URIDINE DERIVATIVE; ALKENE; EPOXIDE; URIDINE;

AMINOHYDROXYLATION; ARTICLE; CRYSTALLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; ELECTROPHILICITY; NUCLEOPHILICITY; OXIDATION; RING OPENING; SHARPLESS EPOXIDATION; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY; X RAY DIFFRACTION; ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ALKENES; EPOXY COMPOUNDS; MOLECULAR STRUCTURE; STEREOISOMERISM; URIDINE; X-RAY DIFFRACTION;

EID: 84906080837     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501410m     Document Type: Article

References (61)

1. De Clercq, E. Annu. Rev. Pharmacol. Toxicol. 2011, 51, 1-24
2. De Clercq, E.; Holy, A. Nat. Rev. Drug Discovery 2005, 4, 928-940
3. Ri, M.; Tashiro, E.; Oikawa, D.; Shinjo, S.; Tokuda, M.; Yokouchi, Y.; Narita, T.; Masaki, A.; Ito, A.; Ding, J.; Kusumoto, S.; Ishida, T.; Komatsu, H.; Shiotsu, Y.; Ueda, R.; Iwawaki, T.; Imoto, M.; Iida, S. Blood Cancer J. 2012, 2, e79
4. Damaraju, V. L.; Damaraju, S.; Young, J. D.; Baldwin, S. A.; Mackey, J.; Sawyer, M. B.; Cass, C. E. Oncogene 2003, 22, 7524-7536
5. Najera, I. Curr. Opin. Virol. 2013, 3, 508-513
6. Jordheim, L. P.; Durantel, D.; Zoulim, F.; Dumontet, C. Nat. Rev. Drug. Discovery 2013, 12, 447-464
7. Takatsuki, A.; Arima, K.; Tamura, G. J. Antibiot. 1971, 24, 215-223
8. Ubukata, M. J. Am. Chem. Soc. 1988, 110, 4416-4417
9. Ubukata, M.; Kimura, K.; Isono, K.; Nelson, C. C.; Gregson, J. M.; McCloskey, J. J. Org. Chem. 1992, 57, 6392-6403
10. Brandish, P. E.; Kimura, K. I.; Inukai, M.; Southgate, R.; Lonsdale, J. T.; Bugg, T. D. Antimicrob. Agents Chemother. 1996, 40, 1640-1644
11. Esumi, Y.; Suzuki, Y.; Kimura, K.; Yoshihama, M.; Ichikawa, T.; Uramoto, M. J. Antibiot. 1999, 52, 281-287
12. Igarashi, M.; Nakagawa, N.; Doi, S.; Hattori, N.; Naganawa, H.; Hamada, M. J. Antibiot. 2003, 56, 580-583
13. Igarashi, M.; Takahashi, Y.; Shitara, T.; Nakamura, H.; Naganawa, H.; Miyake, T.; Akamatsu, Y. J. Antibiot. 2005, 58, 327-337
14. McDonald, L. A.; Barbieri, L. R.; Carter, G. T.; Lenoy, E.; Lotvin, J.; Petersen, P. J.; Siegel, M. M.; Singh, G.; Williamson, R. T. J. Am. Chem. Soc. 2002, 124, 10260-10261
15. Dini, C. Curr. Top. Med. Chem. 2005, 5, 1221-1236
16. Bouhss, A.; Trunkfield, A. E.; Bugg, T. D. H.; Mengin-Lecreulx, D. FEMS Microbiol. Rev. 2008, 32, 208-233
17. Bouhss, A.; Crouvoisier, M.; Blanot, D.; Mengin-Lecreulx, D. J. Biol. Chem. 2004, 279, 29974-29980
18. Gallier, F.; Peyrottes, S.; Périgaud, C. Eur. J. Org. Chem. 2007, 77, 925-933
19. Meurillon, M.; Marton, Z.; Hospital, A.; Jordheim, L. P.; Béjaud, J.; Lionne, C.; Dumontet, C.; Périgaud, C.; Chaloin, L.; Peyrottes, S. Eur. J. Med. Chem. 2014, 77, 18-37
20. Hospital, A.; Meurillon, M.; Peyrottes, S.; Périgaud, C. Org. Lett. 2013, 15, 4778-4781 and references cited therein
21. Besada, P.; Costas, T.; Teijeira, M.; Terán, C. Eur. J. Med. Chem. 2010, 45, 6114-6119
22. Chun, M. W.; Kim, M. J.; Kim, H. O.; Kim, H.-D.; Kim, J. H.; Moon, H. R.; Jeong, L. S. Nucleosides, Nucleotides Nucleic Acids 2003, 22, 915-917
23. Knapp, S.; Morriello, G. J.; Doss, G. A. Org. Lett. 2002, 4, 603-606
24. Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem., Int. Ed. Engl. 1975, 14, 421-422
25. Vorbrüggen, H.; Krolikiewicz, K.; Bennua, B. Chem. Ber. 1981, 114, 1234-1255
26. For a review on nucleosides synthesis: Vorbrüggen, H.; Ruh-Pohlenz, C. Org. React. 2000, 55, 1-630
27. Umino, T.; Minakawa, N.; Matsuda, A. Tetrahedron Lett. 2000, 41, 6419-6423
28. Bligh, C. M.; Anzalone, L.; Jung, Y. C.; Zhang, Y.; Nugent, W. A. J. Org. Chem. 2014, 79, 3238-3243
29. Sarabia, F.; Martín-Ortiz, L.; López-Herrera, F. J. Org. Biomol. Chem. 2003, 1, 3716-3725
30. Ichikawa, S.; Matsuda, A. Nucleosides, Nucleotides Nucleic Acids 2004, 23, 239-253
31. Maturano, M.; Catana, D.-A.; Lavedan, P.; Tarrat, N.; Saffon, N.; Payrastre, C.; Escudier, J.-M. Eur. J. Org. Chem. 2012, 721-730
32. Kim, K. S.; Ahn, Y. H. Tetrahedron: Asymmetry 1998, 9, 3601-3605
33. Gopinath, P.; Wang, L.; Abe, H.; Ravi, G.; Masuda, T.; Watanabe, T.; Shibasaki, M. Org. Lett. 2014, 16, 3364-3367
34. Chen, X.; Wiemer, D. F. J. Org. Chem. 2003, 68, 6597-6604
35. Králíková, Š.; Buděší nký, M.; Masojídková, M.; Rosenberg, I. Tetrahedron 2006, 62, 4917-4932
36. Kurosu, M.; Li, K.; Crick, D. C. Org. Lett. 2009, 11, 2393-2396
37. Lolk, L.; Pøhlsgaard, J.; Jepsen, A. S.; Hansen, L. H.; Nielsen, H.; Steffansen, S. I.; Sparving, L.; Nielsen, A. B.; Vester, B.; Nielsen, P. J. Med. Chem. 2008, 51, 4957-4967
38. Murata, S.; Ichikawa, S.; Matsuda, A. Tetrahedron 2005, 61, 5837-5842
39. Hanessian, S.; Kloss, J.; Sugawara, T. J. Am. Chem. Soc. 1986, 108, 2758-2759
40. Eppacher, S.; Solladié, N.; Bernet, B.; Vasella, A. Helv. Chim. Acta 2000, 83, 1311-1330
41. Spork, A. P.; Koppermann, S.; Ducho, C. Synlett 2009, 15, 2503-2507
42. Spork, P. A.; Koppermann, S.; Dittrich, B.; Herbst-Irmer, R.; Ducho, C. Tetrahedron: Asymmetry 2010, 21, 763-766
43. Sarabia, F.; Vivar-García, C.; García-Ruiz, C.; Martin-Ortiz, L.; Romero-Carasco, A. J. Org. Chem. 2012, 77, 1328-1339
44. Hirano, S.; Ichikawa, S.; Matsuda, A. Angew. Chem., Int. Ed. 2005, 44, 1854-1856
45. Jung, K. Y.; Hohl, R. J.; Wiemer, A. J.; Wiemer, D. F. Bioorg. Med. Chem. 2000, 8, 2501-2509
46. Mvondo, C. E.; Guillerm, G. Tetrahedron Lett. 1996, 37, 163-166
47. Gallier, F.; Alexandre, J. A. C.; El Amri, C.; Deville-Bonne, D.; Peyrottes, S.; Périgaud, C. Chem. Med. Chem. 2011, 6, 1094-1106
48. Lecerclé, D.; Clouet, A.; Al-Dabbagh, B.; Bouhss, A.; Gravier-Pelletier, C.; Le Merrer, Y. Bioorg. Med. Chem. 2010, 18, 4560-4569
49. Mravljak, J.; Monasson, O.; Al-Dabbagh, B.; Crouvoisier, M.; Bouhss, A.; Gravier-Pelletier, C.; Le Merrer, Y. Eur. J. Med. Chem. 2011, 46, 1582-1592
50. Auberger, N.; Frlan, R.; Al-Dabbagh, B.; Bouhss, A.; Crouvoisier, M.; Gravier-Pelletier, C.; Le Merrer, Y. Org. Biomol. Chem. 2011, 9, 8301-8312
51. Fer, M. J.; Olatunji, S.; Bouhss, A.; Calvet-Vitale, S.; Gravier-Pelletier, C. J. Org. Chem. 2013, 78, 10088-10105
52. Lain, L.; Lönnberg, H.; Lönnberg, T. Chem.-Eur. J. 2013, 19, 12424-12434
53. Spork, A. P.; Wiegmann, D.; Granitzka, M.; Stalke, D.; Ducho, C. J. Org. Chem. 2011, 76, 10083-10098
54. Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537-4538
55. Guillarme, S.; Nguyen, T. X. M.; Saluzzo, C. Tetrahedron: Asymmetry 2008, 19, 1450-1454
56. Guthrie, R. D.; Murphy, D. J. Chem. Soc. 1963, 5288-5294
57. Matsuda, K.; Tsuchiya, T.; Torii, T.; Umezawa, S. Bull. Chem. Soc. Jpn. 1986, 59, 1397-1401
58. Zuccarello, G.; Bouzide, A.; Kvarnström, I.; Niklasson, G.; Svensson, S. C. T.; Brisander, M.; Danielsson, H.; Nillroth, U.; Karlén, A.; Hallberg, A.; Classon, B.; Samüelsson, B. J. Org. Chem. 1998, 63, 4898-4906
59. Das, I.; Pathak, T.; Suresh, C. G. J. Org. Chem. 2005, 70, 8047-8054
60. Paz, N. V.; Santana, A. G.; Francisco, C. G.; Suárez, E.; González, C. C. Org. Lett. 2012, 14, 3388-3391
61. Rigolet, S.; McCort, I.; Le Merrer, Y. Tetrahedron Lett. 2002, 43, 8129-8132