2-Allyloxyphenyl glycoside as a new and stable type of glycosyl donors

Tetrahedron Letters

Volumn 47, Issue 10, 2006, Pages 1621-1624

  Lee, Jinq Chyi ^a   Pan, Guan Rong ^a   Kulkarni, Suvarn S ^a   Luo, Shun Yuan ^a   Liao, Chun Chen ^a   Hung, Shang Cheng ^a  

^a NONE

Author keywords

Carbohydrates; Glycoconjugates; Glycosylations

Indexed keywords

2 ALLYLOXYPHENYL GLYCOSIDE; ALCOHOL; GLYCOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; ROOM TEMPERATURE;

EID: 32044463163     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.12.127     Document Type: Article

References (33)

1. A. Varki Glycobiology 3 1993 97
2. J.C. McAuliffe, and O. Hindsgaul Front. Mol. Biol. 30 2000 249
3. H. Paulsen Angew. Chem., Int. Ed. Engl. 21 1982 155
4. R.R. Schmidt Angew. Chem., Int. Ed. Engl. 25 1986 212
5. K. Toshima, and K. Tatsuta Chem. Rev. 93 1993 1503
6. F. Baressi, and O. Hindsgaul B. Ernst C. Leumann Modern Synthetic Methods 1995 VCH Basel, Switzerland 281 330
7. K.M. Koeller, and C.-H. Wong Chem. Rev. 100 2000 4465
8. O.J. Plante, E.R. Palmacci, and P.H. Seeberger Science 291 2001 1523
9. O.J. Plante, E.R. Palmacci, and P.H. Seeberger Adv. Carbohydr. Chem. Biochem. 58 2003 35
10. R.R. Schmidt, and W. Kinzy Adv. Carbohydr. Chem. Biochem. 50 1994 21
11. P.J. Garegg Adv. Carbohydr. Chem. Biochem. 52 1997 179
12. D. Crich, and M. Smith J. Am. Chem. Soc. 123 2001 9015
13. M. Shimizu, H. Togo, and M. Yokoyama Synthesis 1998 799
14. D.R. Mootoo, V. Date, and B. Fraser-Reid J. Am. Chem. Soc. 110 1988 2662
15. D.R. Mootoo, P. Konradsson, U. Udodong, and B. Fraser-Reid J. Am. Chem. Soc. 110 1988 5583
16. B. Fraser-Reid, U.E. Udodong, Z. Wu, H. Ottoson, R. Meritt, C.S. Rao, C. Roberts, and R. Madsen Synlett 1992 927
17. B. Fraser-Reid, and R. Madsen S. Hanessian Preparative Carbohydrate Chemistry 1997 Marcel-Dekker New York 339 356
18. B. Fraser-Reid, G. Anilkumar, M.R. Gilbert, S. Joshi, and R. Kraehmer B. Ernst G.W. Hart P. Sinaÿ Carbohydrates in Chemistry and Biology Vol. 1 2000 Wiley-VCH Weinheim 135 154
19. D. Kahne, S. Walker, Y. Cheng, and D. van Engen J. Am. Chem. Soc. 111 1989 6881
20. J. Gildersleeve, R.A. Pascal Jr., and D. Kahne J. Am. Chem. Soc. 120 1998 5961
21. S.J. Danishefsky, and M.T. Bilodeau Angew. Chem., Int. Ed. 35 1996 1380
22. Z.J. Witczak, and S. Czernecki Adv. Carbohydr. Chem. Biochem. 53 1998 143
23. S. Hashimoto, T. Honda, and S. Ikegami J. Chem. Soc., Chem. Commun. 1989 685
24. Z.Y. Zhang, and C.-H. Wong B. Ernst G.W. Hart P. Sinaÿ Carbohydrates in Chemistry and Biology Vol. 1 2000 Wiley-VCH Weinheim 117 134
25. K.S. Kim, J.H. Kim, Y.J. Lee, Y.J. Lee, and J. Park J. Am. Chem. Soc. 123 2001 8477
26. B.A. Garcia, and D.Y. Gin J. Am. Chem. Soc. 122 2000 4269
27. K. Kitaori, Y. Furukawa, H. Yoshimoto, and J. Otera Adv. Synth. Catal. 343 2001 95
28. C.-A. Tai, S.S. Kulkarni, and S.-C. Hung J. Org. Chem. 68 2003 8719
29. C.-C. Wang, S.-Y. Luo, C.-R. Shie, and S.-C. Hung Org. Lett. 4 2002 847
30. H. Maeta, T. Matsumoto, and K. Suzuki Carbohydr. Res. 249 1993 49
31. J.-C. Lee, X.-A. Lu, S.S. Kulkarni, Y.-S. Wen, and S.-C. Hung J. Am. Chem. Soc. 126 2004 476
32. 4, filtered, and concentrated in vacuo to yield a residue, which was purified by flash column chromatography to provide the desired α-mannopyranosylated adducts (Table 2).
33. Spectral data of selected new compounds