β-Selective glucosylation in the absence of neighboring group participation: influence of the 3,4-O-bisacetal protecting system

Tetrahedron

Volumn 63, Issue 23, 2007, Pages 5042-5049

  Crich, David ^a   Subramanian, Venkataraman ^a   Hutton, Thomas K ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

Bisacetal; Glycosyl triflate; Glycosylation; Protecting group; Stereoselectivity

Indexed keywords

1 BENZENESULFINYL PIPERIDINE; 3,4 O BISACETAL; 3,4 O CARBONATE; ACETAL DERIVATIVE; ACID ANHYDRIDE; CARBONIC ACID; PIPERIDINE DERIVATIVE; THIOGLYCOSIDE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; GLYCOSYLATION; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 34247582306     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.03.128     Document Type: Article

References (40)

1. Review on the effect of cyclic protecting groups in glycosylation:. Litjens R.E.J.N., van den Bos L.J., Codée J.D.C., Overkleeft H.S., and van der Marel G. Carbohydr. Res. 342 (2007) 419-429
2. Crich D., and Lim L.B.L. Org. React. 64 (2004) 115-251
3. Crich D. Chemistry of Glycosyl Triflates: Synthesis of β-Mannopyranosides. In: Wang P.G., and Bertozzi C.R. (Eds). Glycochemistry: Principles, Synthesis, and Applications (2001), Dekker, New York, NY 53-75
4. Crich D. J. Carbohydr. Chem. 21 (2002) 663-686
5. Review on bisacetal chemistry:. Ley S.V., Baeschlin D.K., Dixon D.J., Foster A.C., Ince S.J., Priepke H.W.M., and Reynolds D.J. Chem. Rev. 101 (2001) 53-80
6. Crich D., and Sun S. J. Org. Chem. 62 (1997) 1198-1199
7. Crich D., and Sun S. J. Am. Chem. Soc. 119 (1997) 11217-11223
8. Crich D., and Sun S. Tetrahedron 54 (1998) 8321-8348
9. Rao V.S.R., Qasba P.K., Balaji P.V., and Chandrasekaran R. Conformation of Carbohydrates (1998), Harwood Academic, Amsterdam
10. Grindley T.B. Structure and Conformation of Carbohydrates. In: Fraser-Reid B., Tatsuta K., and Thiem J. (Eds). Glycoscience: Chemistry and Chemical Biology Vol. 1 (2001), Springer, Berlin 3-51
11. Jensen H.H., Nordstrom M., and Bols M. J. Am. Chem. Soc. 126 (2004) 9205-9213
12. Crich D., Cai W., and Dai Z. J. Org. Chem. 65 (2000) 1291-1297
13. Crich D., Vinod A.U., Picione J., and Wink D.J. ARKIVOC (2005) 339-344
14. Crich D., Vinod A.U., and Picione J. J. Org. Chem. 68 (2003) 8453-8458
15. Crich D., and Cai W. J. Org. Chem. 64 (1999) 4926-4930
16. Crich D., and Jayalath P. J. Org. Chem. 70 (2005) 7252-7259
17. Crich D., and Vinogradova O. J. Org. Chem. 71 (2006) 8473-8480
18. Crich D., and Li L. J. Org. Chem. 72 (2007) 1681-1690
19. Crich D., and Smith M. J. Am. Chem. Soc. 123 (2001) 9015-9020
20. Crich D., Banerjee A., Li W., and Yao Q. J. Carbohydr. Chem. 24 (2005) 415-424
21. Crich D., Smith M., Yao Q., and Picione J. Synthesis (2001) 323-326
22. Martín A., Butters T.D., and Fleet G.W.J. Tetrahedron: Asymmetry 10 (1999) 2343-2360
23. Nishio T., Miyake Y., Kubota K., Yamai M., Miki S., Ito T., and Oku T. Carbohydr. Res. 280 (1996) 357-363
24. Paulsen H. Selectivity and Reactivity in Oligosaccharide Synthesis. In: Bartmann W., and Trost B.M. (Eds). Selectivity-A Goal for Synthetic Efficiency (1984), Chemie, Weinheim 169-190
25. Spijker N.M., and van Boeckel C.A.A. Angew. Chem., Int. Ed. Engl. 30 (1991) 180-183
26. Fraser-Reid B., López J.C., Gómez A.M., and Uriel C. Eur. J. Org. Chem. (2004) 1387-1395
27. Veeneman G.H., van Leeuwen S.H., and van Boom J.H. Tetrahedron Lett. 31 (1990) 1331-1334
28. Crich D., de la Mora M., and Vinod A.U. J. Org. Chem. 68 (2003) 8142-8148
29. Crich D., Pedersen C.M., Bowers A.A., and Wink D.J. J. Org. Chem. 72 (2007) 1553-1565
30. Garegg P.J., Hultberg H., and Wallin S. Carbohydr. Res. 108 (1982) 97-101
31. Mootoo D.R., Konradsson P., Udodong U., and Fraser-Reid B. J. Am. Chem. Soc. 110 (1988) 5583-5584
32. Green L.G., and Ley S.V. Protecting Groups: Effects on Reactivity, Glycosylation Stereoselectivity, and Coupling. In: Ernst B., Hart G.W., and Sinaÿ P. (Eds). Carbohydrates in Chemistry and Biology Vol. 1 (2000), Wiley-VCH, Weinheim 427-448
33. Lemieux R.U., Hendriks K.B., Stick R.V., and James K. J. Am. Chem. Soc. 97 (1975) 4056-4062
34. Crich D., and Chandrasekera N.S. Angew. Chem., Int. Ed. 43 (2004) 5386-5389
35. Review on mechanisms of glycoside bond hydrolysis and formation:. Horenstein N.A. Adv. Phys. Org. Chem. 41 (2006) 275-314
36. Nukuda T., Bérces A., Wang L., Zgierski M.Z., and Whitfield D.M. Carbohydr. Res. 340 (2005) 841-852
37. Nukada T., Berces A., and Whitfield D.M. Carbohydr. Res. 337 (2002) 765-774
38. Kim J.-H., Yang H., and Boons G.-J. Angew. Chem., Int. Ed. 44 (2005) 947-949
39. Kim J.-H., Yang H., Park J., and Boons G.-J. J. Am. Chem. Soc. 127 (2005) 12090-12097
40. Smoot J.T., Pornsuriyasak P., and Demchenko A.V. Angew. Chem., Int. Ed. 44 (2005) 7123-7126