One-pot synthesis of penta- and hepta-saccharides from monomeric mannose building blocks using the principles of orthogonality and reactivity tuning

Synlett

Volumn , Issue 4, 1998, Pages 440-442

  Green, Luke ^a   Hinzen, Berthold ^a   Ince, Stuart J ^a   Langer, Peter ^a   Ley, Steven V ^a   Warriner, Stuart L ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 26844574035     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1659     Document Type: Article

References (18)

1. Mizuochi, T.; Spellman, M. W.; Larkin, M.; Soloman, J.; Basa, L. J.; Feizi, T. Biochem. J. 1988, 254, 599.
2. Mootoo, D.R.; Udodong, U.; Konradsson, P.; Fraser-Reid, B. J. Am. Chem. Soc. 1988, 110, 5583.
3. Orthogonal refers to the use of "two chemically distinct glycosyl donors and activation conditions" as defined by Ogawa, T.; Kanie, O.; Ito, Y. J. Am. Chem. Soc. 1994, 116, 12073 and not to the "Orthogonal Glycosylation Strategy" demonstrated therein.
4. Cheung, M-K.; Douglas, N. L.; Hinzen, B.; Ley, S. V.; Pannecoucke, X. Synlett 1997, 257.
5. Others have reported in this area; (a) Raghaven, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580;
6. (b) Yamada, H.; Harada, T.; Miyasaki, H.; Takahashi, T. Tetrahedron Lett. 1994, 35, 3979;
7. (c) Boons, G-J.; Zhu, T. Synlett 1997, 809.
8. a . I.; Echarri, R.; Castillon, S. Synlett 1996, 675.
9. Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503.
10. (a) Douglas, N. L.; Ley, S. V.; Osborn, H. M. I.; Owen, D. R.; Priepke, H. W. M.; Warriner, S. L. Synlett 1996, 793;
11. (b) Montchamp, J-L.; Tian, F.; Hart, M. E.; Frost, J. W. J. Org. Chem. 1996, 61, 3897;
12. (c) Berens, U.; Leckel, D.; Oepen, S. C. J. Org. Chem. 1995, 60, 8204;
13. (d) Douglas, N. L.; Ley, S. V.; Lücking, U.; Warriner, S. L. J. Chem. Soc., Perkin Trans. 1 in press.
14. (a) Suzuki, K.; Maeta, H.; Matsumoto, T. Tetrahedron Lett. 1989, 30, 4856;
15. (b) Ikeshita, S.; Sakamoto, A.; Nakahara, Y.; Ogawa, T. Tetrahedron Lett. 1994, 35, 3123.
16. All new compounds were characterised by spectroscopic and mass data. Preparation of the initial mannose building blocks employed standard protocols which are contained in reference 7d.
17. Veeneman, G. H.; van Leeuwen, S. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 1331.
18. Compound 12 exists a 4:1 α:β mixure of anomers at the position indicated.