Synthesis of C-disaccharides via glucal dimerisation

Tetrahedron Letters

Volumn 37, Issue 50, 1996, Pages 9093-9096

  Byerley, Andrew L J ^a   Kenwright, Alan M ^a   Steel, Patrick G ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DISACCHARIDE; GLUCONATE CALCIUM;

ARTICLE; CHEMICAL REACTION; DIMERIZATION; DRUG SYNTHESIS; POLYMERIZATION; STEREOCHEMISTRY;

EID: 0030577466     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02093-X     Document Type: Article

References (18)

1. 1. Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599.
2. 2. Ferrier, R. J.; Prasad, N. J. Chem. Soc. (C) 1969, 581-586.
3. 3. Similar C-disaccharides in which the two rings are connected by a single bond have also been prepared by: i. radical couplings - Giese, B.; Ruckert, B.; Groninger, K. S.; Muhn, R.; Lindner, H. J. Liebigs Ann. Chem., 1988, 997-1000; Lopez, J. C.; Gomez, A. M.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3871-3878;
4. 3. Similar C-disaccharides in which the two rings are connected by a single bond have also been prepared by: i. radical couplings - Giese, B.; Ruckert, B.; Groninger, K. S.; Muhn, R.; Lindner, H. J. Liebigs Ann. Chem., 1988, 997-1000; Lopez, J. C.; Gomez, A. M.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3871-3878;
5. ii. heteroDiels-Alder reactions of carbohydrate aldehydes-Danishefsky, S. J.; Maring, C. J.; Barbachyn, M. R.; Segmuller, B. E. J. Org. Chem. 1984, 49, 4564-4565; Jurczak, J.; Bauer, T.; Jarosz, S. Tetrahedron Lett. 1984, 25, 4809-4812;
6. ii. heteroDiels-Alder reactions of carbohydrate aldehydes-Danishefsky, S. J.; Maring, C. J.; Barbachyn, M. R.; Segmuller, B. E. J. Org. Chem. 1984, 49, 4564-4565; Jurczak, J.; Bauer, T.; Jarosz, S. Tetrahedron Lett. 1984, 25, 4809-4812;
7. iii. coupling of 1-nitrosugars - Aebischer, B.; Meuwly, R.; Vasella, A. Helv. Chim. Acta. 1984, 67, 2236;
8. iv. reaction of carbohydrate based enol ethers with glucals -Dawe, R. D.; Fraser-Reid, B. J. Org. Chem., 1984, 49, 522;
9. v. homologation from simple C-glycosides - Armstrong, R. W.; Teegarden, B. R. J. Org. Chem., 1992, 57, 915.
10. 4. Miyamoto, M.; Sawamoto, M.; Higashimura, T. Macromolecules 1984, 17, 265; Sawamoto, M.; Okamoto, C.; Higashimura, T. Macromolecules 1987, 20, 2693.
11. 4. Miyamoto, M.; Sawamoto, M.; Higashimura, T. Macromolecules 1984, 17, 265; Sawamoto, M.; Okamoto, C.; Higashimura, T. Macromolecules 1987, 20, 2693.
12. 5. Ogawa, Y.; Sawamoto, M.; Higashimura, T. Polymer J. 1984, 16, 415.
13. 6. Subsequent X-ray diffraction on dimer (17) has confirmed this assignment. Details of the X-ray study will be given in the full paper.
14. 7. Humoller, F.L. Methods Carbohydr. Chem. 1962, 1, 83.
15. 8. Danishefsky, S. J.; Kerwin, J. F.; Kobayashi, S. J. Am. Chem. Soc. 1982, 104, 358.
16. 9. All new compounds were fully characterised giving satisfactory spectral and analytical data. All yields refer to pure isolated products.
17. 1H-COSY, nOe, one bond and long range HETCOR]. To the best of our knowledge this rearrangemnt of a glucal derivative is unprecedented. The highly functionalised cyclopentane product has great potential in synthesis eg. as a precursor to carbocyclic nucleosides. The scope of this process and synthetic applications of the products are currently under study and the results obtained will be reported in due course.
18. 11. Larsen, E.; Jørgenscn, P. T.; Sofan, M. A.; Pedersen, E.B. Synthesis 1994, 1037.