Propargyl 1,2-orthoesters as glycosyl donors: stereoselective synthesis of 1,2-trans glycosides and disaccharides

Tetrahedron Letters

Volumn 48, Issue 37, 2007, Pages 6564-6568

  Sureshkumar, Gopalsamy ^a   Hotha, Srinivas ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DIOXOLENIUM ION; ALIPHATIC COMPOUND; AURIUM BROMIDE; BROMINE DERIVATIVE; DISACCHARIDE; ESTER DERIVATIVE; GLYCOSIDE; GOLD DERIVATIVE; ION; LEWIS ACID; STEROID; SUGAR ALCOHOL; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; GLYCOSIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 34547790218     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.07.015     Document Type: Article

References (65)

1. Rudd P.M., Elliott T., Cresswell P., Wilson I.A., and Dwek R.A. Science 291 (2001) 2370-2376
2. McAuliffe J.C., and Hindsgaul O. Front. Mol. Biol. 30 (2000) 249-285
3. Varki A. Glycobiology 3 (1993) 97-130
4. Dwek R.A. Chem. Rev. 96 (1996) 683-720
5. Roy R. In: Boons G.J. (Ed). Carbohydrate Chemistry (1998), Chapman and Hall, UK 243-321
6. Kiessling L.L., and Pohl N.L. Chem. Biol. 3 (1996) 71-77
7. Bovin N.J., and Gabius H.-J. Chem. Soc. Rev. 24 (1995) 413-421
8. Gordon E.J., Sanders W.J., and Kiessling L.L. Nature 392 (1998) 30-31
9. Koeller K.M., and Wong C.-H. Chem. Rev. 100 (2000) 4465-4494
10. Ragupathi G., Koide F., Livingston P.O., Cho Y.S., Endo A., Wan Q., Spassova M.K., Keding S.J., Allen J., Ouerfelli O., Wilson R.M., and Danishefsky S.J. J. Am. Chem. Soc. 128 (2006) 2715-2725
11. Plante O.J., Palmacci E.R., and Seeberger P.H. Adv. Carbohydr. Chem. Biochem. 58 (2003) 35-44
12. Nguyen H.M., Chen Y., Duron S.G., and Gin D.Y. J. Am. Chem. Soc. 123 (2001) 8766-8772
13. Toshima K., and Tatsuta K. Chem. Rev. 93 (1993) 1503-1531
14. Schmidt R.R. Angew. Chem., Int. Ed. Engl. 25 (1986) 212-235
15. Paulsen H. Angew. Chem., Int. Ed. Engl. 21 (1982) 155-173
16. Schmidt R.R., and Kinzy W. Adv. Carbohydr. Chem. Biochem. 50 (1994) 21-123
17. Shimizu M., Togo H., and Yokoyama M. Synthesis (1998) 799-822
18. Kahne D., Walker S., Cheng Y., and van Engen D. J. Am. Chem. Soc. 111 (1989) 6881-6882
19. Danishefsky S.J., and Biolodeau M.T. Angew. Chem., Int. Ed. 35 (1996) 1380-1419
20. Witczak Z.J., and Czernecki S. Adv. Carbohydr. Chem. Biochem. 53 (1998) 143-199
21. Hashimoto S., Honda T., and Ikegami S. J. Chem. Soc., Chem. Commun. (1989) 685-687
22. Zhang Z.Y., and Wong C.-H. In: Ernst B., Hart G.W., and Sinaÿ P. (Eds). Carbohydrates in Chemistry and Biology Vol. 1 (2000), Wiley-VCH, Weinheim 117-134
23. Mootoo D.R., Date V., and Fraser-Reid B. J. Am. Chem. Soc. 110 (1988) 2662-2663
24. Garegg P.J. Adv. Carbohydr. Chem. Biochem. 52 (1997) 179-205
25. Crich D., and Smith M. J. Am. Chem. Soc. 123 (2001) 9015-9020
26. Demchenko A.V., Pornsuriyasak P., Meo C.D., and Malysheva N.N. Angew. Chem., Int. Ed. 43 (2004) 3069-3072
27. Kim J.H., Yang H., and Boons G.-J. Angew. Chem., Int. Ed. 44 (2005) 947-949
28. Kim K.S., Kim J.H., Lee Y.J., Lee Y.J., and Park J. J. Am. Chem. Soc. 123 (2001) 8477-8481
29. Kim J.-H., Yang H., and Boons G.-J. Angew. Chem., Int. Ed. 44 (2005) 947-949
30. Kim J.-H., Yang H., Park J., and Boons G.-J. J. Am. Chem. Soc. 127 (2005) 12090-12097
31. Boons G.-J. Contemp. Org. Synth. 3 (1996) 173-200
32. Roberts C., Madsen R., and Fraser-Reid B. J. Am. Chem. Soc. 117 (1995) 1546-1553
33. Allen J.G., and Fraser-Reid B. J. Am. Chem. Soc. 121 (1999) 468-469
34. Jayaprakash K.N., Radhakrishnan K.V., and Fraser-Reid B. Tetrahedron Lett. 43 (2002) 6953-6955
35. Fraser-Reid B., Grimme S., Piacenza M., Mach M., and Schlueter U. Chem. Eur. J. 9 (2003) 4687-4692
36. Bamhaoud T., Sanchez S., and Prandi J. J. Chem. Soc., Chem. Commun. (2000) 659-660
37. Radhakrishnan K.V., Sajisha V.S., and Chacko J.M. Synlett (2005) 997-999
38. King J.F., and Allbutt A.D. Can. J. Chem. 48 (1970) 1754-1769
39. Deslongchamps P. Stereoelectronic Effects in Organic Chemistry (1983), Pergamon Press, New York Chapter 3
40. Bochkov A.F., and Zaikov G.E. Chemistry of the O-Glycosidic Bond (1979), Pergamon Press, Oxford, U.K. Chapter 2, 5-79
41. Hotha S., and Kashyap S. J. Am. Chem. Soc. 128 (2006) 9620-9621
42. Hotha S., and Kashyap S. J. Org. Chem. 71 (2006) 364-367 and 852
43. Hotha S., and Kashyap S. Tetrahedron Lett. 47 (2006) 2021-2023
44. Maurya S.K., and Hotha S. Tetrahedron Lett. 47 (2006) 3307-3310
45. Hotha S., and Tripathi A. J. Comb. Chem. 7 (2005) 968-976
46. Hashmi A.S.K., Frost T.M., and Bats J.W. J. Am. Chem. Soc. 122 (2000) 11553-11554
47. Hashmi A.S.K., Ding L., Bats J.W., Fischer P., and Frey W. Chem. Eur. J. 9 (2003) 4339-4345
48. Asao N., Aikawa H., and Yamamoto Y. J. Am. Chem. Soc. 126 (2004) 7458-7459
49. Arcade A., Bianchi G., and Marinelli F. Synthesis (2004) 610-618
50. Yao T., Zhang X., and Larock R.C. J. Am. Chem. Soc. 126 (2004) 11164-11165
51. Staben S.T., Kennedy-Smith J.J., and Toste F.D. Angew. Chem., Int. Ed. 43 (2004) 5350-5352
52. Nieto-Oberhuber C., Munoz M.P., Bunuel E., Nevado C., Cardenas D.J., and Echavarren A.M. Angew. Chem., Int. Ed. 43 (2004) 2402-2406
53. Zhang L., and Kozmin S.A. J. Am. Chem. Soc. 127 (2005) 6962-6963
54. Yao X., and Li C.-J. J. Am. Chem. Soc. 126 (2004) 6884-6885
55. Shi Z., and He C. J. Am. Chem. Soc. 126 (2004) 5964-5965
56. Shi Z., and He C. J. Org. Chem. 69 (2004) 3669-3671
57. Shi X., Gorin D.J., and Toste F.D. J. Am. Chem. Soc. 127 (2005) 5802-5803
58. Hoffmann-Röder A., and Krause N. Org. Biomol. Chem. 3 (2005) 387-391
59. Jiménez-Núñez E., and Echavarren A.M. Chem. Commun. (2007) 333-346 and references cited therein
60. 5d.
61. Kochetkov K., Klimov E.M., Malysheva N.N., and Demchenko A.V. Carbohydr. Res. 212 (1991) 77-91
62. Kochetkov K., Zhuin V.M., Klimov E.M., Malysheva N.N., Makarova Z.G., and Ott A.Y. Carbohydr. Res. 164 (1987) 241-254
63. Mach M., Schlueter U., Mathew F., Fraser-Reid B., and Hazen K.C. Tetrahedron 58 (2002) 7345-7354
64. 13C, DEPT NMR and CHNS analysis as well as mass spectrometry. See Supplementry data.
65. 3 (10 mol %) under argon at room temperature. The reaction mixture was stirred at room temperature for the specified time and then filtered and the filtrate concentrated in vacuo. The resulting residue was purified by silica gel column chromatography using ethyl acetate-petroleum ether as the mobile phase.