Protecting of a thermolabile protecting group: "click-clack" approach

Organic Letters

Volumn 11, Issue 16, 2009, Pages 3742-3745

  Chmielewski, Marcin K ^a  

^a INSTITUTE OF BIOORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOPHOSPHORUS COMPOUND; OXAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; METHODOLOGY; ORGANIC CHEMISTRY; SYNTHESIS;

CHEMISTRY, ORGANIC; CYCLIZATION; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS; OXAZOLES;

EID: 68949113866     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901358d     Document Type: Article

References (20)

1. Lemmen, P.; Richter, W.; Werner, B.; Karl, R.; Stumpf, R.; Ugi, I. Synthesis 1993, 1, 12.
2. Iyer, R. P.; Yu, D.; Devlin, T.; Ho, N.; Agraval, S. J. Org. Chem. 1995, 60, 5388-5389.
3. Stec, W. J.; Grajkowski, A.; Koziołkiewicz, M.; Uznanski, B. Nucleic Acids Res. 1991, 19, 5883-5888.
4. Wilk, A.; Grajkowski, A.; Phillips, L. R.; Beaucage, S. L. J. Am. Chem. Soc. 2000, 122, 2149-2156.
5. Wilk, A.; Grajkowski, A.; Phillips, L. R.; Beaucage, S. L. J. Org. Chem. 1999, 64, 7515-7522.
6. Grajkowski, A.; Wilk, A.; Chmielewski, M. K.; Phillips, L. R.; Beaucage, S. L. Org. Lett. 2001, 3, 1287-1290.
7. Wilk, A.; Chmielewski, M. K.; Grajkowski, A.; Phillips, L. R.; Beaucage, S. L. J. Org. Chem. 2002, 67, 6430-6438.
8. Grajkowski, A.; Cieslak, J.; Chmielewski, M. K.; Marchan, V.; Phillips, L. R.; Wilk, A.; Beaucage, S. L. Ann. N.Y. Acad. Sci. 2003, 1002, 1-11.
9. Wilk, A.; Grajkowski, A.; Chmielewski, M. K.; Phillips, L. R.; Beaucage, S. L. Tetrahedron Lett. 2001, 42, 5635-5639.
10. Chmielewski, M. K.; Marchan, V.; Cieslak, J.; Grajkowski, A.; Livengood, V.; Munch, U.; Wilk, A.; Beaucage, S. L. J. Org. Chem. 2003, 68, 10003-10012.
11. Weiner, N.; Kaye, I. A. J. Org. Chem. 1949, 14, 868-872.
12. Beaucage, S. L.; Chmielewski, M. K. PCT Int. Appl. WO200410158 2, 2004.
13. Cieslak, J.; Beaucage, S. L. J. Org. Chem. 2003, 68, 10123-10129.
14. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021.
15. In the presence of water and acid, the 3-pyridyl-[1,3,2]oxazaphos- pholidine 3 was easily transformed into an 3-pyridyl-[1,3,2]oxaza- H-phospholidin-2-one.
16. The hydrolysis under alkaline conditions it led to cleavage of the P-O bonds without thermolabile properties of this group. Treatment of 5 with strong bases like DBU leads to several products with thymidin-3′-yl N-(2-pyridyl-2-hydroxyethyl) H-phosphonamidate being a main product.
17. Stawiński, J.; Stromberg, R.; Zain, R. Tetrahedron Lett. 1992, 33, 3185-3188.
18. Kraszewski, A.; Sobkowski, M.; Stawiński, J. J. Chem. Soc., Perkin Trans. 1 1993, 1, 1699-1704.
19. Hata, T.; Sekine, M. Tetrahedron Lett. 1974, 3943.
20. Sekine, M.; Yamagata, H.; Hata, T. Tetrahedron Lett. 1979, 375.