Propargyloxycarbonyl (Poc) as a Protective Group for the Hydroxyl Function in Carbohydrate Synthesis

Organic Letters

Volumn 4, Issue 26, 2002, Pages 4731-4733

  Sridhar, Perali Ramu ^a   Chandrasekaran, S ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0442264158     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027220x     Document Type: Article

References (34)

1. (a) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; DeRoose, F. J. Am. Chem. Soc. 1997, 119, 449 and references therein.
2. (b) Osborn, H. M. I.; Khan, T. H. Tetrahedron 1999, 55, 1807.
3. (c) Ling, R.; Yan, L.; Loebach, J.; Ge, M.; Uozumi, Y.; Sekanina, K.; Horan, N.; Gildersleeve, J.; Thompson, C.; Smith, A.; Biswas, K.; Still, W. C.; Khane, D. Science 1996, 274, 1520.
4. (d) Zhu, T.; Boons, G. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1898.
5. For recent reviews, see: (a) Arya, P.; Ben, R. N. Angew Chem., Int. Ed. Engl. 1997, 36, 1280. (b) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1432.
6. For recent reviews, see: (a) Arya, P.; Ben, R. N. Angew Chem., Int. Ed. Engl. 1997, 36, 1280. (b) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1432.
7. Sinha, S.; Ilankumaran, S.; Chandrasekaran, S. Tetrahedron Lett. 1999, 40, 771.
8. Adinolfi, M.; Barone, G.; Guariniello, L.; Iadonisi, A. Tetrahedron Lett. 2000, 41, 9305.
9. Johansson, R.; Samuelsson, B. J. Chem. Soc., Perkin Trans. 1 1984, 2371.
10. (a) Wuensch, E.; Gref, W.; Keller, O.; Keller, W.; Wersin, G. Synthesis 1986, 11, 958.
11. (b) Munegumi, T.; Meng, Y.-Q.; Harada, K. Bull. Chem. Soc. Jpn. 1989, 62, 2748.
12. (c) Schmidt, U.; Kroner, M.; Beutler, U. Synthesis 1988, 6, 475.
13. (a) Teshima, T.; Nakajima, K.; Takahashi, M.; Shiba, T. Tetrahedron Lett. 1992, 33, 363.
14. (b) Depre, D.; Düffels, A.; Green, L. G.; Lenz, R.; Ley, S. V.; Wong, C.-H. Chem. Eur. J. 1999, 5, 3326.
15. (c) Kobayashi, Y.; Ishida, N.; Arai, M.; Shiozaki, M.; Hiraoka, T. Carbohydr. Res. 1991, 222, 83.
16. (d) Dondoi, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. Synthesis 1998, 685.
17. (e) Fukase, K.; Kinoshita, I.; Kanoh, T.; Nakai, Y.; Hasuoka, A.; Kusumoto, S. Tetrahedron 1996, 52, 3897.
18. Guibe, F.; Saint M'Leux, Y. Tetrahedron Lett. 1981, 22, 3591.
19. Harada, T.; Yamada, H.; Tsukamoto, H.; Takahashi, T. J. Carbohydr. Chem. 1995, 14, 165.
20. Dominique, L.; Boullanger, P.; Bonoub, J.; Descotes. G. Can. J. Chem. 1990, 68, 828.
21. Dangles O.; Guibe, F.; Balavoine, G.; Lavielle, S.; Marquet, A. J. Org. Chem. 1987, 52, 4984.
22. Hayakawa, Y.; Wakabayashi, S.; Kato, H. Noyori, R. J. Am. Chem. Soc. 1990, 112, 1691.
23. Wong, C.-H.; Ye, X. S.; Zhang, Z. J. Am. Chem. Soc. 1998, 120, 7137.
24. Boullanger, P.; Banoub, J.; Descotes, G. Can. J. Chem. 1987, 65, 1343.
25. (a) Zhu, T.; Boons, G.-J. J. Am. Chem. Soc. 2000, 122, 10222.
26. (b) Zhu, T.; Boons, G. J. Chem. Eur. J. 2001, 7, 2382.
27. (c) Konradsson, P.; Udodong. U.; Fraser-Reid, B. Tetrahedron Lett. 1990, 31, 4313.
28. (d) Veeneman, G. H.; van Leeuwen, S. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 1331.
29. (a) Schmidt, R. R.; Michel, J. Angew. Chem., Int. Ed. Engl. 1980, 19, 731.
30. (b) Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212.
31. (a) Schene, H.; Waldmann, H. Eur. J. Org. Chem. 1998, 1227.
32. (b) Takeo, K.; Tei, S. Carbohydr. Res. 1986, 145, 307.
33. The Poc protective group is not stable under catalytic hydrogenation conditions.
34. Bell, D. J.; Lorber, J. J. Chem. Soc. 1940, 453.