Stereoselective N -glycosylation of 2-deoxythioribosides for fluorescent nucleoside synthesis

Journal of Organic Chemistry

Volumn 77, Issue 20, 2012, Pages 9006-9017

  Mata, Guillaume ^a   Luedtke, Nathan W ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

HIGH YIELD; IN-SITU; LOW-YIELD; NUCLEOBASES; PROTECTING GROUP; PYRIMIDINE DERIVATIVES; QUINAZOLINES; STEREO-SELECTIVE; THIOGLYCOSIDES;

FLUORESCENCE; SULFUR;

BIOMOLECULES;

2 DEOXYTHIORIBOSIDE DERIVATIVE; 4 TOLYL 3 O 4 METHOXYBENZOYL 1 THIO 5 O TRIISOPROPYLSILYL 2 DEOXY ALPHA, BETA DEXTRO RIBOFURANOSIDE; 4 TOLYL 3 O(N ACETYL)GLYCYL 1 THIO 5 O TRIISOPROPYLSILYL 2 DEOXY ALPHA, BETA DEXTRO RIBOFURANOSIDE; 4 TOLYL 3,5 DI O 4 TOLUO 1 THIO 2 DEOXY ALPHA, BETA DEXTRO RIBOFURANOSIDE; 4 TOLYL 3,5 DI O ACETYL 1 THIO 2 DEOXY ALPHA, BETA DEXTRO RIBOFURANOSIDE; 4 TOLYL 3,5 O (DI TERT BUTYLSILYLENE) 1 THIO 2 DEOXY ALPHA, BETA DEXTRO RIBOFURANOSIDE; 4 TOLYL 3,5 O (TETRAISOPROPYLSILOXANE 1,3 DIYL) 1 THIO 2 DEOXY ALPHA, BETA DEXTRO RIBOFURANOSIDE; 5 TOLYL 3 O ACETYL 1 THIO 5 O TRIISOPROPYLSILYL 2 DEOXY ALPHA, BETA DEXTRO RIBOFURANOSIDE; 5 TOLYL 3 O BENZOYL 1 THIO 5 O TRIISOPROPYLSILYL 2 DEOXY ALPHA, BETA DEXTRO RIBOFURANOSIDE; HYDROXYL GROUP; NUCLEIC ACID BASE; NUCLEOSIDE; OXOPHENOTHIAZINE; PYRIMIDINE DERIVATIVE; QUINAZOLINE; SULFUR; THIOGLYCOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; GLYCOSYLATION; SILYLATION; STEREOCHEMISTRY;

DEOXYRIBOSE; FLUORESCENT DYES; GLYCOSYLATION; MOLECULAR STRUCTURE; NUCLEOSIDES; STEREOISOMERISM; THIOGLYCOSIDES;

EID: 84867725244     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3014929     Document Type: Article

References (51)

1. Zhang, L.-H.; Xi, Z.; Chattopadhyaya, J. Medicinal Chemistry of Nucleic Acids; John Wiley & Sons, Inc.: Hoboken, NJ, 2011.
2. Vittori, S.; Dal Ben, D.; Lambertucci, C.; Marucci, G.; Volpini, R.; Cristalli, G. Curr. Med. Chem. 2006, 13, 3529
3. De Clercq, E. Med. Res. Rev. 2008, 28, 929
4. Uhlmann, E.; Peyman, A. Chem. Rev. 1990, 90, 543
5. Englisch, U.; Gauss, D. H. Angew. Chem., Int. Ed. 1991, 30, 613
6. Cobb, A. J. A. Org. Biomol. Chem. 2007, 5, 3260
7. Sinkeldam, R. W.; Greco, N. J.; Tor, Y. Chem. Rev. 2010, 110, 2579
8. Luedtke, N. W.; Dumas, A. J. Am. Chem. Soc. 2010, 132, 18004
9. Salic, A.; Mitchison, T. J. Proc. Natl. Acad. Sci. U. S. A. 2008, 105, 2415
10. Neef, A. B.; Luedtke, N. W. Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 20404
11. Chien, T. C.; Chen, C. S.; Chern, J. W. J. Chin. Chem. Soc. 2005, 52, 1237
12. Fossey, C.; Landelle, H.; Laduree, D.; Robba, M. Nucleosides Nucleotides 1994, 13, 925
13. Tor, Y.; Del Valle, S.; Jaramillo, D.; Srivatsan, S. G.; Rios, A.; Weizman, H. Tetrahedron 2007, 63, 3608
14. Liu, H. B.; Gao, J. M.; Kool, E. T. J. Org. Chem. 2005, 70, 639
15. Robins, M. J.; Wilson, J. S. J. Am. Chem. Soc. 1981, 103, 932
16. Seela, F.; Debelak, H. Nucleosides Nucleotides Nucleic Acids 2001, 20, 577
17. Park, M.; Rizzo, C. J. J. Org. Chem. 1996, 61, 6092
18. Wang, Z. W.; Prudhomme, D. R.; Buck, J. R.; Park, M.; Rizzo, C. J. J. Org. Chem. 2000, 65, 5969
19. Wang, Z. W.; Rizzo, C. J. Org. Lett. 2000, 2, 227
20. Kazimierczuk, Z.; Cottam, H. B.; Revankar, G. R.; Robins, R. K. J. Am. Chem. Soc. 1984, 106, 6379
21. Arico, J. W.; Calhoun, A. K.; McLaughlin, L. W. J. Org. Chem. 2010, 75, 1360
22. Kotick, M. P.; Szantay, C.; Bardos, T. J. J. Org. Chem. 1969, 34, 3806
23. Rolland, V.; Kotera, M.; Lhomme, J. Synth. Commun. 1997, 27, 3505
24. Hubbard, A. J.; Jones, A. S.; Walker, R. T. Nucleic Acids Res. 1984, 12, 6827
25. Michel, J.; Gueguen, G.; Vercauteren, J.; Moreau, S. Tetrahedron 1997, 53, 8457
26. Godde, F.; Toulme, J. J.; Moreau, S. Biochemistry 1998, 37, 13765
27. Hurley, L. H.; Kendrick, S.; Akiyama, Y.; Hecht, S. M. J. Am. Chem. Soc. 2009, 131, 17667
28. Tor, Y.; Shin, D. W. J. Am. Chem. Soc. 2011, 133, 6926
29. Pan, M. Y.; Hang, W.; Zhao, X. J.; Zhao, H.; Deng, P. C.; Xing, Z. H.; Qing, Y.; He, Y. Org. Biomol. Chem. 2011, 9, 5692
30. Sandin, P.; Lincoln, P.; Brown, T.; Wilhelmsson, L. M. Nat. Protoc. 2007, 2, 615
31. Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503
32. Schmidt, R. R. Angew. Chem., Int. Ed. 1986, 25, 212
33. van der Marel, G. A.; Codee, J. D. C.; Litjens, R. E. J. N.; van den Bos, L. J.; Overkleeft, H. S. Chem. Soc. Rev. 2005, 34, 769
34. Crich, D.; Smith, M. J. Am. Chem. Soc. 2001, 123, 9015
35. Crich, D.; Pedersen, C. M.; Bowers, A. A.; Wink, D. J. J. Org. Chem. 2007, 72, 1553
36. Young, R. J.; Shawponter, S.; Hardy, G. W.; Mills, G. Tetrahedron Lett. 1994, 35, 8687
37. Hashimoto, S.; Inagaki, J.; Sakamoto, H.; Sano, A.; Nakajima, M. Heterocycles 1997, 46, 215
38. Sujino, K.; Sugimura, H. Chem. Lett. 1993, 1187
39. Sandin, P.; Wilhelmsson, L. M.; Lincoln, P.; Powers, V. E. C.; Brown, T.; Albinsson, B. Nucleic Acids Res. 2005, 33, 5019
40. Vorbruggen, H.; Krolikiewicz, K.; Bennua, B. Chem. Ber./Recl. 1981, 114, 1234
41. Vorbruggen, H. Acc. Chem. Res. 1995, 28, 509
42. Niedball., U; Vorbrugg., H. J. Org. Chem. 1974, 39, 3654
43. Kurosu, M.; Li, K. J. Org. Chem. 2008, 73, 9767
44. Liu, Z. G.; Li, D. Y.; Yin, B. L.; Zhang, J. C. Tetrahedron Lett. 2010, 51, 240
45. Ishiwata, A.; Akao, H.; Ito, Y. Org. Lett. 2006, 8, 5525
46. Mootoo, D. R.; Konradsson, P.; Udodong, U.; Fraserreid, B. J. Am. Chem. Soc. 1988, 110, 5583
47. Sandin, P.; Wilhelmsson, M.; Lincoln, P.; Norden, B.; Albinsson, B. Biophys. J. 2005, 88, 410a
48. Larsen, C. H.; Ridgway, B. H.; Shaw, J. T.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 12208
49. Larsen, C. H.; Ridgway, B. H.; Shaw, J. T.; Smith, D. M.; Woerpel, K. A. J. Am. Chem. Soc. 2005, 127, 10879
50. Smith, D. M.; Tran, M. B.; Woerpel, K. A. J. Am. Chem. Soc. 2003, 125, 14149
51. Xie, Y.; Dix, A. V.; Tor, Y. J. Am. Chem. Soc. 2009, 131, 17605