Stereocontrolled access to carba-C-disaccharides via functionalized dienylsilanes

Tetrahedron Letters

Volumn 38, Issue 51, 1997, Pages 8845-8848

  Angelaud, Rémy ^a   Landais, Yannick ^a   Parra Rapado, Liliana ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; GLYCOSIDASE INHIBITOR;

ARTICLE; CARBOHYDRATE SYNTHESIS; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030812725     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10389-6     Document Type: Article

References (23)

1. (a) Winchester, B.; Fleet, G.W.J. Glycobiology, 1992, 2, 199-210;
2. (b) Humphries, M.J.; Matsumoto, K.; White, S.L.; Olden, K. Proc. Natl. Acad. Sci. U.S.A., 1986, 46, 1752-1756;
3. (c) Anzeveno, P.B.; Creemer, L.J.; Daniel, J.K.; King, C.-H.R.; Liu, P.S. J. Org. Chem., 1989, 54, 2539-2542.
4. (a) Sinott, M.L. Chem. Rev., 1990, 90, 1171-1202;
5. (b) Legler, G. Adv. Carbohydr. Chem., 1990, 48, 319-384.
6. For comprehensive reviews on the total synthesis of C-glycosides, see: (a) Postema, M.H.D. Tetrahedron, 1992, 48, 8545-8599;
7. (b) Levy, D.E.; Tang, C. in The Chemistry of C-Glycosides, Tetrahedron Organic Chemistry series, Pergamon, Elsevier Science Ltd., 1995.
8. (a) Lesimple, P.; Beau, J.-M; Sinaÿ, P.J. Carbohydr. Res., 1987, 171, 289-300;
9. (b) See also: Wittmann, V.; Kessler, H. Angew. Chem. Int. Ed. Engl., 1993, 32, 1091-1093.
10. Reichelt, I.; Reissig, H.-U. Liebigs, Ann. Chem., 1984, 828-830.
11. Fleming, I.; Dunoguès, J.; Smithers, R. Org. React., 1989, 37, 57-575.
12. (a) Preceding communication in this issue;
13. (b) Angelaud, R.; Landais, Y. J. Org. Chem., 1996, 61, 5202-5203.
14. The Schiff-base was prepared from benzaldehyde and ethylenediamine, following our reported procedure: Andrey, O.; Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron, 1995, 51, 12083-12096.
15. 1H NMR indicated that using this procedure, less than 5% of the undesired vinylsilanes were formed.
16. 4, resulted in the formation of the desired cyclopropane in good yield but with no enantioselectivity. See: (a) Pfaltz, A. Acc. Chem. Res., 1993, 26, 339-345;
17. (b) Evans, D.A.; Woerpel, K.A.; Scott, M.J. Angew. Chem. Int. Ed. Engl., 1992, 31, 430-432;
18. (c) Protopopova, M.N.; Doyle, M.P.; Müller, P.; Ene, D. J. Am. Chem. Soc., 1992, 114, 2755-2757.
19. The anti configuration was attributed to 12a having the diol moiety trans relative to the silicon group. The lower diastereocontrol in the cyclopentadienyl series may be attributed to the close proximity of the cyclopropane moiety and the approaching osmium reagent which forces, to a certain extent, the dihydroxylation to proceed syn relative to the silicon group. Such a trend was not observed with cyclohexadienyl systems, where cyclopropanation, followed by dihydroxylation, afforded a single diastereomer, both processes occurring anti relative to the silicon group.
20. Landais, Y.; Parra-Rapado, L. Tetrahedron Lett., 1996, 37, 1209-1212 and references cited therein.
21. As indicated by the oxidation with PDC, 16a,c is a 80:5 mixture of the aldol epimers at C7 (implying a 88% d.e. for the aldolisation), formed from the major enantiomer of the pseudo-sugar 9. The third aldol 16b, obtained pure after chromatography (15%), is thus generated from the minor enantiomer of 9, in good agreement with the enantiomeric excess measured for 5 (71% e.e.).
22. 1H NMR studies.
23. 1H NMR studies unambiguously showed that retention of configuration at the anomeric centre occurred during the aldol-oxidation sequence leading to 18a-b, similarly to what was observed for the preparation of 17.