Is an acyl group at O-3 in glucosyl donors able to control α-stereoselectivity of glycosylation? the role of conformational mobility and the protecting group at O-6

Carbohydrate Research

Volumn 384, Issue , 2014, Pages 70-86

  Komarova, Bozhena S ^a   Orekhova, Maria V ^a   Tsvetkov, Yury E ^a   Nifantiev, Nikolay E ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

3 O Acetyl group; Glucosyl N phenyltrifluoroacetimidate; Glucosyl sulfoxide; Glycosylation; Remote anchimeric participation; Stereodirecting effect

Indexed keywords

STEREOSELECTIVITY;

3-O-ACETYL GROUP; CONFORMATIONAL MOBILITY; GLUCOSYL N-PHENYLTRIFLUOROACETIMIDATE; GLUCOSYL SULFOXIDE; REACTION TEMPERATURE; REMOTE ANCHIMERIC PARTICIPATION; STANDARD CONDITIONS; STEREO-SELECTIVE;

GLYCOSYLATION;

ACETIC ACID DERIVATIVE; BENZYL DERIVATIVE; GLUCAN; OLIGOSACCHARIDE; SULFOXIDE; IMIDOESTER; SAFROLE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; CONFORMATION; CONTROLLED STUDY; GLYCOSYLATION; PRIORITY JOURNAL; STEREOCHEMISTRY; TEMPERATURE; ANALOGS AND DERIVATIVES; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CARBOHYDRATE CONFORMATION; GLYCOSYLATION; IMIDOESTERS; OLIGOSACCHARIDES; SAFROLE; STEREOISOMERISM;

EID: 84896539406     PISSN: 00086215     EISSN: 1873426X     Source Type: Journal    
DOI: 10.1016/j.carres.2013.11.016     Document Type: Article

References (68)

1. S. Aubry, K. Sasaki, I. Sharma, and D. Crich Top. Curr. Chem. 301 2011 141 188
2. S. Manabe Methods Enzymol. 478 2010 413 435
3. J.Y. Baek, B.-Y. Lee, M.G. Jo, and K.S. Kim J. Am. Chem. Soc. 131 2009 17705 17713
4. H.H. Jensen, L.U. Nordstrøm, and M. Bols J. Am. Chem. Soc. 126 2004 9205 9213
5. V.K. Srivastava, and C. Schuerch J. Org. Chem. 46 1981 1121 1126
6. R.E.J.N. Litjens, L.J. van den Bos, J.D.C. Codée, H.S. Overkleeft, and G.A. van der Marel Carbohydr. Res. 342 2007 419 429
7. J.D.C. Codée, L.J. van den Bos, A.-R. de Jong, J. Dinkelaar, G. Lodder, H.S. Overkleeft, and G.A. van der Marel J. Org. Chem. 74 2009 38 47
8. L. Ayala, C.G. Lucero, J.A.C. Romero, S.A. Tabacco, and K.A. Woerpel J. Am. Chem. Soc. 125 2003 15521 15528
9. S. Manabe, and Y. Ito Curr. Bioact. Comp. 4 2008 258 281
10. J.D.C. Codée, A.R. de Jong, J. Dinkelaar, H.S. Overkleeft, and G.A. van der Marel Tetrahedron 65 2009 3780 3788
11. D. Crich Acc. Chem. Res. 43 2010 1144 1153
12. A.V. Demchenko Synlett 2003 1225 1240
13. B.S. Komarova, N.E. Ustyuzhanina, Y.E. Tsvetkov, and N.E. Nifantiev Stereocontrol of 1,2-cis-Glycosylation by Remote O-Acyl Protecting Groups S. Vidal, D. Wertz, Modern Synthetic Methods in Carbohydrate Chemistry - From Monosaccharides to Complex Glycoconjugates 2014 Wiley-VCH 125 159
14. N.E. Ustyuzhanina, V.B. Krylov, A.A. Grachev, A.G. Gerbst, and N.E. Nifantiev Synthesis 23 2006 4017 4031
15. B.S. Komarova, Y.E. Tsvetkov, Y.A. Knirel, U. Zähringer, G.B. Pier, and N.E. Nifantiev Tetrahedron Lett. 47 2006 3583 3587
16. B.S. Komarova, Y.E. Tsvetkov, G.B. Pier, and N.E. Nifantiev J. Org. Chem. 73 2008 8411 8421
17. B.S. Komarova, Y.E. Tsvetkov, G.B. Pier, and N.E. Nifantiev Carbohydr. Res. 360 2012 56 68
18. M.G. Beaver, S.B. Billings, and K.A. Woerpel J. Am. Chem. Soc. 130 2008 2082 2086
19. D. Crich, T. Hu, and F. Cai J. Org. Chem. 73 2008 8942 8953
20. A.G. Gerbst, N.E. Ustuzhanina, A.A. Grachev, E.A. Khatuntseva, D.E. Tsvetkov, D.M. Whitfield, A. Berces, and N.E. Nifantiev J. Carbohydr. Chem. 20 2001 821 831
21. D. Crich, and S. Sun J. Org. Chem. 61 1996 4506 4507
22. D. Crich, and Q. Yao J. Am. Chem. Soc. 126 2004 8232 8236
23. D. Crich, and I. Sharma J. Org. Chem. 75 2010 8383 8391
24. D. Crich, and S. Sun J. Am. Chem. Soc. 120 1998 435 436
25. D. Crich, and S. Sun J. Org. Chem. 62 1997 1198 1199
26. G. Stork, and J.J. La Clair J. Am. Chem. Soc. 118 1996 247 248
27. D. Crich, W. Li, and H. Li J. Am. Chem. Soc. 126 2004 15081 15086
28. C.M. Gampe, H. Tsukamoto, T.-S.A. Wang, S. Walker, and D. Kahne Tetrahedron 67 2011 9771 9778
29. D. Crich, H. Li, Q. Yao, D.J. Wink, R.D. Sommer, and A.L. Rheingold J. Am. Chem. Soc. 123 2001 5826 5828
30. C.M. Gampe, H. Tsukamoto, E.H. Doud, S. Walker, and D. Kahne J. Am. Chem. Soc. 135 2013 3776 3779
31. Y. Zhang, E.J. Fechter, T.-S.A. Wang, D. Barrett, S. Walker, and D.E. Kahne J. Am. Chem. Soc. 129 2007 3080 3081
32. M.A. Walczak, and S.J. Danishefsky J. Am. Chem. Soc. 134 2012 16430 16433
33. S. Koto, Y. Takebe, and S. Zen Bull. Chem. Soc. Jpn. 45 1972 291 293
34. A. Pastore, S. Valerio, M. Adinolfi, and A. Iadonisi Chem. Eur. J. 17 2011 5881 5889
35. F. Good, and C. Schuerch Carbohydr. Res. 125 1984 165 171
36. S. Koto, N. Morishima, K. Takenaka, K. Kanemitsu, N. Shimoura, M. Kase, S. Kojiro, T. Nakamura, T. Kawase, and N. Zen Bull. Chem. Soc. Jpn. 62 1989 3549 3566
37. Z. Zhang, and B. Yu J. Org. Chem. 68 2003 6309 6313
38. M. Adinolfi, G. Barone, A. Iadonisi, and M. Schiattarella Tetrahedron Lett. 43 2002 5573 5577
39. M. Nitz, and D.R. Bundle J. Org. Chem. 65 2000 3064 3073
40. H. Qin, and T.B. Grindley J. Carbohydr. Chem. 15 1996 95 108
41. Z. Zhang, C. Zong, G. Song, G. Lv, Y. Chun, P. Wang, N. Ding, and Y. Li Carbohydr. Res. 345 2010 750 760
42. K. Daragics, and P. Fügedi Tetrahedron 66 2010 8036 8046
43. F. Dasgupta, and P.J. Garegg Acta Chem. Scand. 43 1989 471 475
44. A.M.P. Steijn, J.P. Kamerling, and J.F.G. Vliegenthart Carbohydr. Res. 225 1992 229 246
45. P. Pornsuriyasak, and A.V. Demchenko Chem. Eur. J. 12 2006 6630 6646
46. W. Yang, J. Sun, W. Lu, Y. Li, L. Shan, W. Han, W.-D. Zhang, and B. Yu J. Org. Chem. 75 2010 6879 6888
47. P. Bohn, N. Le Fur, G. Hagues, J. Costentin, N. Torquet, C. Papamicäel, F. Marsaisa, and V. Levacher Org. Biomol. Chem. 7 2009 2612 2618
48. A.B. Smith III, R.A. Rivero, K.J. Hale, and H.A. Vaccaro J. Am. Chem. Soc. 113 1991 2092 2112
49. V. Krylov, N. Ustyuzhanina, H. Bakker, and N. Nifantiev Synthesis 2007 3147 3154
50. N. Ustyuzhanina, B. Komarova, N. Zlotina, V. Krylov, A. Gerbst, Y. Tsvetkov, and N. Nifantiev Synlett 2006 921 923
51. D. Crich, and W. Cai J. Org. Chem. 64 1999 4926 4930
52. D. Crich, and A.U. Vinod J. Org. Chem. 70 2005 1291 1296
53. D. Crich, M. de la Mora, and A.U. Vinod J. Org. Chem. 68 2003 8142 8148
54. D. Crich, and M. Smith Org. Lett. 2 2000 4067 4069
55. K.S. Kim, J.H. Kim, Y.J. Lee, Y.J. Lee, and J. Park J. Am. Chem. Soc. 123 2001 8477 8481
56. W.F.J. Hogendorf, L.J. Van den Bos, H.S. Overkleeft, J.D.C. Codée, and G.A. Van der Marel Bioorg. Med. Chem. 18 2010 3668 3678
57. L. Legnani, S. Ronchi, S. Fallarini, G. Lombardi, F. Campo, L. Panza, L. Lay, L. Poletti, L. Toma, F. Ronchetti, and F. Compostell Org. Biomol. Chem. 7 2009 4428 4436
58. Y. Bai, and T.L. Lowary J. Org. Chem. 71 2006 9672 9680
59. E.C. Lourenço, D. Maycock, and M.R. Ventura Carbohydr. Res. 344 2009 2073 2078
60. D. Crich, and L. Li J. Org. Chem. 72 2007 1681 1690
61. J. Kalikanda, and Zh. Li J. Org. Chem. 76 2011 5207 5218
62. M. Heuckendorff, C.M. Pedersen, and M. Bols J. Org. Chem. 77 2012 5559 5568
63. D. Crich, and M. Smith J. Am. Chem. Soc. 123 2001 9015 9020
64. D. Crich, and S. Sun Tetrahedron 54 1998 8321 8348
65. D. Crich, and S. Sun J. Am. Chem. Soc. 119 1997 11217 11223
66. N.M. Spijker, and C.A.A. van Boeckel Angew. Chem., Int. Ed. 30 1991 180 183
67. M. Andreas, and E. Ulf J. Org. Chem. 69 2004 6249 6256
68. S. Garneau, L. Qiao, L. Chen, S. Walker, and J.C. Vederas Bioorg. Med. Chem. 12 2004 6473 6494