Stereoselective synthesis of 1,2-13C2-L-fucose, 1,2-13C2-fucono-γ-lactone and 1,2- 13C2-fucono-γ-lactol from non-sugar starting material

Synlett

Volumn , Issue 17, 2005, Pages 2685-2687

  Gardiner, John M ^a   Panchal, Nitesh R ^a   Stimpson, William T ^a   Herbert, John M ^b   Ellames, George J ^b  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b Alnwick Research Centre   (United Kingdom)

Author keywords

Carbohydrates; Isotope labelled; Stereoselective synthesis

Indexed keywords

1,2 FUCONO GAMMA LACTOL; 1,2 FUCONO GAMMA LACTONE; 1,2 LEVO FUCOSE; CARBON 13; OLIGOSACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; CYCLIZATION; DEPROTECTION REACTION; DIHYDROXYLATION; ISOTOPE LABELING; REDUCTION; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 27444435650     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-917071     Document Type: Article

References (23)

1. (a) Meyer, B.; Weimar, T.; Peters, T. Eur. J. Biochem. 1997, 246, 705.
2. (b) Haselhorst, T.; Espinosa, J. F.; Jimenez-Barbero, J.; Sokolowski, T.; Kosma, P.; Brade, H.; Brade, L.; Peters, T. Biochemistry 1999, 38, 6449.
3. (c) Mayer, M.; Meyer, B. J. Med. Chem. 2000, 43, 2093.
4. Mayer, M.; Meyer, B. J. Am. Chem. Soc. 2001, 123, 6108.
5. van Halbeek, H. Curr. Opin. Struct. Biol. 1994, 4, 697.
6. Snyder, J. R.; Serianni, A. S. Carbohydr. Res. 1987, 163, 169.
7. Hayes, M. L.; Pennings, N. J.; Serianni, A. S.; Barker, R. J. Am. Chem. Soc. 1982, 104, 6764.
8. (a) Wendeborn, S.; Nussbaumer, S.; Hannes, R. F.; Joerg, M.; Pachlatko, J. P. Tetrahedron Lett. 2002, 43, 31.
9. (b) Xu, Z.; Johannes, C. W.; Salman, S. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 10926.
10. 2O).
11. Matsumoto, T.; Hosoya, T.; Suzuki, K. J. Am. Chem. Soc. 1992, 114, 3568.
12. Balitz, D. M.; O'Herron, F. A.; Bush, J.; Vyas, D. M.; Netiletron, D. E.; Grulich, R. E.; Bradner, W. T.; Doyle, T. W.; Arnold, E.; Clardy, J. J. Antibiot. 1981, 34, 1544.
13. Jain, T. C.; Simolike, G. C.; Jackman, L. M. Tetrahedron Lett. 1983, 39, 599.
14. 13 This reaction has also been carried out on multi-gram scale.
15. (a) Takahasi, S.; Kuzuhara, H. J. Chem. Soc., Perkin Trans. 1 1997, 607.
16. (b) Kinoshita, T.; Miwa, T.; Clardy, J. Carbohydr. Res. 1985, 143, 249.
17. (c) Angyal, S. J.; Pickles, V. A. Aust. J. Chem. 1972, 25, 1695.
18. McNaught, A. D. Pure Appl. Chem. 1996, 68, 1919.
19. The unlabelled peracylated analogue of 7 has been described, prepared by homologation from the precursor C5 aldehyde: Shunya Takahashi, S.; Kuzuhara, H. J. Chem. Soc., Perkin Trans, 1 1997, 607.
20. 2-labelled compounds.
21. 3).
22. (a) Kinoshita, T.; Miwa, T.; Clardy, J. Carbohydr. Res. 1985,143, 249.
23. (b) Allavudeen, S. S.; Kuberan, B.; Loganathan, D. Carbohydr. Res. 2002, 337, 965.