An efficient approach for the synthesis of 1′-O-α-methyl pyrrolo[2,3-d]pyrimidine isonucleosides

Synthesis

Volumn , Issue 8, 2011, Pages 1213-1218

  Song, Yang ^a   Yang, Ruchun ^b   Ding, Haixin ^b   Sun, Qi ^b   Xiao, Qiang ^b   Ju, Yong ^a  

^a TSINGHUA UNIVERSITY   (China)

^b JIANGXI SCIENCE AND TECHNOLOGY NORMAL UNIVERSITY   (China)

Author keywords

Csium carbonate; Ionucleoside; Prrolo 2,3 d pyrimidine; Rgioselective deprotection; Tiflate

Indexed keywords

CSIUM CARBONATE; DEPROTECTION; IONUCLEOSIDE; PRROLO[2,3-D]PYRIMIDINE; TIFLATE;

CARBONATION; CESIUM;

AROMATIC COMPOUNDS;

3 (METHYL ALPHA DEXTRO ARABINOFURANOSID 2 YL)ADENINE; 4 AMINO 7 (METHYL ALPHA DEXTRO ARABINOFURANOSID 2 YL) 7H PYRROLO[2,3 D]PYRIMIDINE; 4 METHOXY 7 (METHYL ALPHA DEXTRO ARABINOFURANOSID 2 YL) 7H PYRROLO[2,3 D]PYRIMIDINE; 7 (METHYL ALPHA DEXTRO ARABINOFURANOSID 2 YL) 3,7 DIHYDRO 4H PYRROLO[2,3 D]PYRIMIDIN 4 ONE; NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL COMPOSITION; CHEMICAL MODIFICATION; DEPROTECTION REACTION; DRUG SYNTHESIS; NUCLEIC ACID BASE SUBSTITUTION; STEREOCHEMISTRY;

EID: 79953774299     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1259961     Document Type: Article

References (47)

1. Nakamura G, J. Antibiot. 1961 14A 90
2. Nishimura H, Katagiri K, Sato K, Mayama M, Shimaoka N T., J. Antibiot. 1956 9A 60
3. Ohkuma K, J. Antibiot., Ser. A 1961 14 343
4. Seela F, Peng X H., Curr. Top. Med. Chem. 2006 6 867
5. Seela F, Peng X H., Budow S, Curr. Org. Chem. 2007 11 427
6. Kim Y A., Sharon A, Chu C K., J. Med. Chem. 2008 51 3934
7. Changelian P S., Flanagan M E., Ball D, Kent C R., Borie D C., Science 2003 302 875
8. Bundy G L., Ayer D E., Banitt L S., Belonga K L., Mizsak S A., Palmer J R., Tustin J M., Chin J E., Hall E D., Linseman K L., Richards I M., Scherch H M., Sun F F., Yonkers P A., Larson P G., Lin J M., Padbury G E., Aaron C S., Mayo J K., J. Med. Chem. 1995 38 4161
9. Montgomery J A., Clayton S D., Thomas H J., J. Org. Chem. 1975 40 1923
10. Montgomery J A., Thomas H J., J. Org. Chem. 1978 43 541
11. Bobek M, An S.-H, Skrincosky D, De Clercq E, Bernacki R J., J. Med. Chem. 1989 32 799
12. Huryn D M., Sluboski B C., Tam S Y., Weigele M, Sim I, Anderson B D., Mitsuya H, Brodert S, J. Med. Chem. 1992 35 2347
13. Tino J A., Clark J M., Field A K., Jacobs G A., Lis K A., Michalik T L., McGeever-Rubin B, Slusarchyk W A., Spergel S H., Sundeen J E., Tuomari A V., Weaver E R., Young M G., Zahler R, J. Med. Chem. 1993 36 1221
14. Franchetti P, Cappellacci L, Grifantini M, Memini L, Sheikha G A., Loi A G., Tramontano E, De Mantis A, Spiga M G., La Colla P, J. Med. Chem. 1994 37 3534
15. Alexander P, Krishnamurthy V V., Prisbe E J., J. Med. Chem. 1996 39 1321
16. Yu H W., Zhang L R., Zhou J C., Ma L T., Zhang L H., Bioorg. Med. Chem. 1996 4 609
17. Jin D Z., Kwon S H., Moon H R., Gunaga P, Kim H O., Kim D.-K, Chun M W., Jeong L S., Bioorg. Med. Chem. 2004 12 1101
18. Guenther S, Balzarini J, De Clercq E, Nair V, J. Med. Chem. 2002 45 5426
19. Talekar R R., Wightman R H., Tetrahedron 1997 53 3831
20. Jung M E., Toyota A, Tetrahedron Lett. 2000 41 3577
21. Tian X B., Min J M., Zhang L H., Tetrahedron: Asymmetry 2000 11 1877
22. Jung M E., Nichols C J., J. Org. Chem. 1998 63 347
23. Lei Z, Min J M., Zhang L H., Tetrahedron: Asymmetry 2000 11 2899
24. Bera S, Mickle T, Nair V, Nucleosides Nucleotides 1999 18 2379
25. Lou C G., Xiao Q, Brennan L, Light M E., Vergara-Irigaray N, Atkinson E M., Holden-Dye L M., Fox K R., Brown T, Bioorg. Med. Chem. 2010 18 6389
26. Martin P, Helv. Chim. Acta 1995 78 486
27. Martin O R., Kurz K G., Rao S P., J. Org. Chem. 1987 52 2922
28. Li N S., Lu J, Piccirilli J A., Org. Lett. 2007 9 3009
29. Hori H, Nishida Y, Ohrui H, Meguro H, J. Org. Chem. 1989 54 1346
30. Lecourt T, Hrault A, Pearce A J., Sollogoub M, Siny P, Chem. Eur. J. 2004 12 2960
31. Jia C, Zhang Y M., Zhang L H., Siny P, Sollogoub M, Carbohydr. Res. 2006 341 2135
32. Seela F, Kretschmer U, J. Heterocycl. Chem. 1990 27 479
33. Seela F, Westermann B, Bindig U, J. Chem. Soc., Perkin Trans. 1 1988 697
34. Ugarkar B G., Castellino A J., DaRe J M., Kopcho J J., Wiesner J B., Schanzer J M., Erion M D., J. Med. Chem. 2000 43 2894
35. Ugarkar B G., Castellino A J., DaRe J S., Ramirez-Weinhouse M, Kopcho J J., Rosengren S, Erion M D., J. Med. Chem. 2003 46 4750
36. Tian X B., Min J M., Zhang L H., Tetrahedron: Asymmetry 2000 11 1877
37. Bera S, Nair V, Tetrahedron 2001 42 5813
38. Rosemeyer H, Seela F, Helv. Chim. Acta 1988 71 1573
39. Bhattacharya B K., Rao T S., Revankar G R., J. Chem. Soc., Perkin Trans. 1 1995 1543
40. Nair V, Piotrowska D G., Okello M, Vadakkan J, Nucleosides Nucleotides 2007 26 687
41. Bouisset T, Gosselin G, Griffe L, Meillon J C., Storer R, Tetrahedron 2008 64 6657
42. Galli C, Org. Prep. Proced. Int. 1992 24 287
43. Flessner T, Doye S, J. Prak. Chem./Chem. Ztg. 1999 341 186
44. Su T L., Klein R S., Fox J J., J. Org. Chem. 1981 46 1790
45. Salvatore R N., Nagele A S., Jung K W., J. Org. Chem. 2002 67 674
46. Seela F, Peng X H., J. Org. Chem. 2006 71 81
47. Seela F, Ming X, Tetrahedron 2007 63 9850