Preparation, structure, derivatisation and NMR data of cyclohexane-1,2-diacetal protected carbohydrates

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 4, 1997, Pages 351-363

  Grice, Peter ^a   Ley, Steven V ^a   Pietruszka, Jörg ^a   Priepke, Henning W M ^a   Warriner, Stuart L ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748652692     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a605851e     Document Type: Article

References (30)

1. P. Grice, S. V. Ley, J. Pietruszka and H. W. M. Priepke, Angew. Chem., Int. Ed. Engl., 1996, 35, 197.
2. S. V. Ley, R. Downham, P. J. Edwards, J. E. Innes and M. Woods, Contemp. Org. Synth., 1995, 2, 365.
3. S. V. Ley, H. W. M. Priepke and S. L. Warriner, Angew. Chem., Int. Ed. Engl., 1994, 33, 2290.
4. N. L. Douglas, S. V. Ley, H. M. I. Osborn, D. R. Owen, H. W. M. Priepke and S. L. Warriner, Synlett, 1996, 793.
5. S. V. Ley and H. W. M. Priepke, Angew. Chem., Int. Ed. Engl., 1994, 33, 2292.
6. Cyclohexane-1,2-dione and 1,1,2,2-tetramethoxycyclohexane are both available from Avocado Research Chemicals, Shore Road, Port of Heysham Industrial Park, Heysham, Lancashire LA3 2XY, England.
7. M. Bouchra, P. Calinaud and J. Gelas, Carbohydr. Res., 1995, 267, 227.
8. Atomic coordinates, bond lengths and angles, and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre (CCDC). For details of the deposition scheme, see 'Instructions for Authors', J. Chem. Soc., Perkin Trans. 1, 1997, Issue 1. Any request to the CCDC for this material should quote the full literature citation and the reference number 207/68.
9. Methyl α-D-mannopyranoside: (a) B. M. Gatehouse and B. J. Poppleton, Acta Crystallogr., Sect. B, 1970, 26, 1761;
10. (b) G. A. Jeffrey, R. K. McMulle and S. T. Akagi, Acta Crystallogr., Sect. B, 1977, 33, 728.
11. Man-α(1,2)-Man-α(1)-OMe disaccharide: T. Srikrishnan, M. S. Chowdhary and K. L. Matta, Carbohydr. Res., 1989, 186, 167.
12. K. Bock and J. Duus, J. Carbohydr. Chem., 1994, 13, 513.
13. M. E. Evans and F. W. Parrish, Carbohydr. Res., 1977, 54, 105.
14. (a) J. G. Buchanan, M. E. Chacon-Fuertes, A. R. Edgar, S. J. Moorehouse, D. I. Rawson and R. H. Wightman, Tetrahedron Lett., 1980, 21, 1793;
15. (b) J. G. Buchanan, A. R. Edgar, D. I. Rawson, P. Shahidi and R. H. Wightman, Carbohydr. Res., 1982, 100, 75.
16. T. Ogawa and K. Sasajima, Carbohydr. Res., 1981, 93, 67.
17. For the 1-O-allyl compound see also: H. Paulson and B. Helpap, Carbohydr. Res., 1991, 216, 289.
18. J. Thiem, V. Duckstein, A. Prahst and M. Matzke, Liebigs Ann. Chem., 1987, 289.
19. TIPDS protection was developed by Markiewicz: W. T. Markiewicz, J. Chem. Res. (S), 1979, 24.
20. P. Grice, S. V. Ley, J. Pietruszka, H. W. M. Priepke and E. P. E. Walther, Synlett, 1995, 781.
21. J. F. Stoddart, Stereochemistry of Carbohydrates, Wiley Interscience, New York, 1971, p. 68.
22. V. Waagen, T. K. Barua, H. W. Anthonsen, L. K. Hansen, D. J. Fossli, E. Hough and T. Anthonsen, Tetrahedron, 1994, 50, 10056.
23. For 3,4-dibenzyl-protected rhamnosides see: (a) O-methyl: V. Pozsgay, J. R. Brisson and H. J. Jennings, Can. J. Chem., 1987, 65, 2764;
24. (b) For S-methyl rhamnoside see: V. Pozsgay and H. J. Jennings, J. Org. Chem., 1988, 53, 4042.
25. H. M. Flowers, Carbohydr. Res., 1982, 100, 418.
26. P. J. Garegg and B. Samuelsson, J. Chem. Soc., Perkin Trans. 1, 1980, 2866.
27. T. L. Arsenault, D. B. MacLean, W. Zou and W. A. Szarek, Can. J. Chem., 1994, 72, 1376.
28. G. Stork and G. Kim, J. Am. Chem. Soc., 1992, 114, 1087.
29. M. Bols, J. Chem. Soc., Chem. Commun., 1993, 791.
30. D. E. Wright, Tetrahedron, 1979, 35, 1207.