Sequential one-pot glycosylation with glycosyl N-trichloroacetylcarbamate and trichloroacetate including dehydrative approach using 1-hydroxy sugars

Tetrahedron

Volumn 67, Issue 35, 2011, Pages 6482-6496

  Shirahata, Tatsuya ^a   Kojima, Asami ^a   Teruya, Satoko ^a   Matsuo, Jun Ichi ^b,c   Yokoyama, Masaki ^a   Unagiike, Shogo ^a   Sunazuka, Toshiaki ^a   Makino, Kazuishi ^a   Kaji, Eisuke ^a   Omura, Satoshi ^a   Kobayashi, Yoshinori ^a  

^a KITASATO UNIVERSITY   (Japan)

^b KITASATO INSTITUTE   (Japan)

^c KANAZAWA UNIVERSITY   (Japan)

Author keywords

Dehydrative approach; Glycosylation; Sequential one pot glycosylation

Indexed keywords

2,3,4 TRI O BENZOYL 6 O (2,3,4,6 TETRA O BENZYL ALPHA,BETA DEXTRO GLUCOPYRANOSYL) ALPHA DEXTRO GLUCOPYRANOSIDE; 2,3,4 TRI O BENZYL 6 O 4 METHOXYBENZYL ALPHA DEXTRO MANNOPYRANOSE; 2,3,4 TRI O BENZYL 6 O 4 METHOXYBENZYL ALPHA,BETA DEXTRO GALACTOPYRANOSE; 2,3,4 TRI O BENZYL 6 O 4 METHOXYBENZYL ALPHA,BETA DEXTRO GALACTOPYRANOSYL TRICHLOROACETATE; 2,3,4 TRI O BENZYL 6 O 4 METHOXYBENZYL ALPHA,BETA DEXTRO GLUCOPYRANOSYL TRICHLOROACETATE; 2,3,4 TRI O BENZYL 6 O 4 METHOXYBENZYL ALPHA,BETA DEXTRO MANNOPYRANOSYL TRICHLOROACETATE; 2,3,4 TRI O BENZYL ALPHA DEXTRO GALACTOPYRANOSYL TRICHLOROACETATE; 2,3,4 TRI O BENZYL ALPHA,BETA DEXTRO GLUCOPYRANOSYL TRICHLOROACETATE; 2,3,4 TRI O BENZYL ALPHA,BETA DEXTRO MANNOPYRANOSYL TRICHLOROACETATE; 2,3,4,6 TETRA O BENZYL ALPHA,BETA DEXTRO GALACTOPYRANOSYL TRICHLOROACETATE; 2,3,4,6 TETRA O BENZYL ALPHA,BETA DEXTRO MANNOPYRANOSYL TRICHLOROACETATE; 2,3,4,6 TETRA O BENZYL DEXTRO GLUCOPYRANOSYL TRICHLOROACETATE; CARBAMIC ACID DERIVATIVE; CARBOHYDRATE DERIVATIVE; GALACTOSE; GLUCOSE; GLYCOSYL N TRICHLOROACETYLCARBAMATE; LEWIS ACID; MANNOSE; METHYL 2,3,4 TRI O BENZOYL 6 O (2,3,4,6 TETRA O BENZYL ALPHA,BETA DEXTRO GALACTOPYRANOSYL) ALPHA DEXTRO GALACTOPYRANOSIDE; METHYL 2,3,4 TRI O BENZOYL 6 O (2,3,4,6 TETRA O BENZYL ALPHA,BETA DEXTRO MANNOPYRANOSYL) ALPHA DEXTRO MANNOPYRANOSIDE; METHYL 2,3,4,5 TETRA O BENZYL ALPHA DEXTRO MANNOPYRANOSYL (1-6) 2,3,4 TRI O BENZYL ALPHA DEXTRO MANNOPYRANOSYL (1-6) 2,3,4 TRI O BENZOYL ALPHA DEXTRO MANNOPYRANOSIDE; METHYL 2,3,4,6 TETRA O BENZYL ALPHA DEXTRO GALACTOPYRANOSYL (1-6) 2,3,4 TRI O BENZYL ALPHA DEXTRO GALACTOPYRANOSYL (1-6) 2,3,4 TRI O BENZOYL ALPHA DEXTRO GALACTOPYRANOSIDE; METHYL 2,3,4,6 TETRA O BENZYL ALPHA DEXTRO GLUCOPYRANOSYL (1-6) 2,3,4 TRI O BENZYL ALPHA DEXTRO GLUCOPYRANOSYL (1-6) 2,3,4 TRI O BENZOYL ALPHA DEXTRO GLUCOPYRANOSIDE; PHENYL 2,3,4 TRI O BENZOYL 6 O 4 METHOXYBENZYL 1 THIO ALPHA DEXTRO MANNOPYRANOSIDE; PHENYL 2,3,4 TRI O BENZYL 6 O 4 METHOXYBENZYL 1 THIO BETA DEXTRO GALACTOPYRANOSIDE; TRICHLOROACETIC ACID; TRISACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; GLYCOSYLATION; PRIORITY JOURNAL; SEQUENTIAL ONE POT GLYCOSYLATION; SYNTHESIS; TEMPERATURE;

EID: 79960957868     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.06.006     Document Type: Article

References (43)

1. P. Stallforth, B. Lepenies, A. Adibekian, and P.H. Seeberger J. Med. Chem. 52 2009 5561 5577
2. B. Ernst, and J.L. Magnani Nat. Rev. Drug Discov. 8 2009 661 677
3. D.P. Galonic, and D.Y. Gin Nature 446 2007 1000 1007
4. P.H. Seeberger, and D.B. Werz Nature 446 2007 1046 1051
5. A.V. Demchenko Handbook of Chemical Glycosylation 2008 Wiley-VCH Weinheim
6. X. Zhu, and R.R. Schmidt Angew. Chem., Int. Ed. 48 2009 1900 1934
7. T.J. Boltje, and T. Buskas Nat. Chem. 1 2009 611 622
8. H. Tanaka, H. Yamada, and T. Takahashi Trends Glycosci. Glycotechnol. 19 2007 183 193
9. O. Kanie, Y. Ito, and T. Ogawa J. Am. Chem. Soc. 116 1994 12073 12074
10. Y. Yamada, T. Kato, and T. Takahashi Tetrahedron Lett. 40 1999 4581 4584
11. D.R. Mootoo, P. Konradsson, U. Udodong, and B. Fraser-Reid J. Am. Chem. Soc. 110 1988 5583 5584
12. B. Fraser-Reid, Z. Wu, U.E. Udodong, and H. Ottosson J. Org. Chem. 55 1990 6068 6070
13. Z. Zhang, I.R. Ollmann, X.-S. Ye, R. Wischnat, T. Baasov, and C.-H. Wong J. Am. Chem. Soc. 121 1999 734 753
14. M. Adinolfi, A. Iadonisi, and A. Ravid Synlett 2006 583 586
15. S. Valerio, A. Pastore, M. Adinolfi, and A. Iadonisi J. Org. Chem. 73 2008 4496 4503
16. J. Matsuo, T. Shirahata, and S. Omura Tetrahedron Lett. 47 2006 267 271
17. T. Shirahata, J. Matsuo, S. Teruya, N. Hirata, T. Kurimoto, N. Akimoto, T. Sunazuka, E. Kaji, and S. Omura Carbohydr. Res. 345 2010 740 749
18. Z.-J. Li, H.-Q. Huang, and M.-S. Cai J. Carbohydr. Chem. 15 1996 501 506
19. M. Wakao, Y. Nakai, K. Fukase, and S. Kusumoto Chem. Lett. 1999 27 28
20. Y.-P. Lu, H. Li, M.-S. Cai, and Z.-J. Li Carbohydr. Res. 334 2001 289 294
21. X.-X. Zhu, P.Y. Ding, and M.-S. Cai Tetrahedron: Asymmetry 7 1996 2833 2838
22. M. Bindl, L. Jean, J. Herrmann, R. Müller, and A. Fürstner Chem. - Eur. J. 15 2009 12310 12319
23. 10 2,3,4-benzyloxy acceptor and 2,3,4-benzoyloxy acceptor have similar reactivity as acceptors, in this reason, 2,3,4-benzoyloxy acceptor 3 was used
24. H. Nagai, K. Sasaki, S. Matsumura, and K. Toshima Carbohydr. Res. 340 2005 337 353
25. G. Wulff, and G. Rohle Angew. Chem., Int. Ed. Engl. 13 1974 157 170
26. Y. Nakahara, and T. Ogawa Carbohydr. Res. 200 1990 363 375
27. M. Kreuzer, and J. Thiem Carbohydr. Res. 149 1986 347 361
28. C. Uriel, A.M. Gomez, J.C. Lopez, and B. Fraser-Reid J. Carbohydr. Chem. 24 2005 665 675
29. P. Blom, B. Ruttens, S.V. Hoof, I. Hubrecht, and J.V. Eycken J. Org. Chem. 70 2005 10109 10112
30. C. Shie, Z. Tzeng, S.S. Kulkarni, B. Uang, C. Hsu, and S. Hung Angew. Chem., Int. Ed. 44 2005 1665 1668
31. X. He, and T.H. Chan Synthesis 10 2006 1645 1651
32. E. Sisu, M. Sollogoub, J.M. Mallet, and P. Sinay Tetrahedron 58 2002 10189 10196
33. A. Esmurziev, E. Sundby, and B.H. Hoff Eur. J. Org. Chem. 2009 1592 1597
34. K. Kawahira, H. Tanaka, A. Ueki, Y. Nakahara, H. Hojo, and Y. Nakahara Tetrahedron 65 2009 8143 8153
35. S. Deng, U. Gangadharmath, and C.-W.T. Chang J. Org. Chem. 71 2006 5179 5185
36. Z.T. Li, and J.C. Gildersleeve J. Am. Chem. Soc. 128 2006 11612 11619
37. M.S.M. Timmer, B.L. Stocker, P.T. Northcote, and B.A. Burkett Tetrahedron Lett. 50 2009 7199 7204
38. A.J. Janczuk, W. Zhang, P.R. Andreana, J. Warrick, and P.G. Wang Carbohydr. Res. 337 2002 1247 1259
39. N. Khiar, and M. Martin-Lomas J. Org. Chem. 60 1995 7017 7021
40. G.D.K. Kumar, and S. Baskaran J. Org. Chem. 70 2005 4520 4523
41. G. Lemanski, and T. Ziegler Tetrahedron 56 2000 563 579
42. F.S. Ekholm, M. Poláková, A.J. Pawłowicz, and R. Leino Synthesis 4 2009 567 576
43. B.A. Garcia, and D.Y. Gin J. Am. Chem. Soc. 122 2000 4269 4279