Collect. Czech. Chem. Commun. 2005, 70, 2086-2100
https://doi.org/10.1135/cccc20052086

Conformational Preferences of Ethyl 2,3-Dideoxy-3-[(α-D-glucopyranosyl)methyl]-β-L- and -D-arabino-hexopyranosides

Ondřej Vícha, Ladislav Kniežoa,*, Hana Dvořákováb, Ivan Raicha and Štěpán Valentaa

a Department of Chemistry of Natural Compounds, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic
b NMR Laboratory, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic

References

1a. Fraser-Reid B. O., Tatsuta K., Thiem J. (Eds): Glycoscience: Chemistry and Chemical Biology. Springer-Verlag, Heidelberg 2001.
1b. Ernst B., Hart G. W., Sinaÿ P. (Eds): Carbohydrates in Chemistry and Biology. Wiley–VCH, Weinheim 2000.
2a. Levy D. E., Tang C. in: The Chemistry of C-Glycosides, Tetrahedron Organic Chemistry Series (J. E. Baldwin and P. D. Magnus, Eds). Pergamon–Elsevier Science, Oxford 1995.
2b. Postema M. H. D.: C-Glycoside Synthesis. CRC, Boca Raton (FL) 1995.
2c. Vogel P., Ferrito R., Kraehenbuehl K., Baudat A. in: Carbohydrate Mimics, Concept and Methods (Y. Chapleur, Ed.), p. 19. Wiley–VCH, Weinheim 1998.
2d. Du Y., Linhardt R. J., Vlahov I. R.: Tetrahedron 1998, 54, 9913. <https://doi.org/10.1016/S0040-4020(98)00405-0>
2e. Vogel P.: Chimia 2001, 55, 359.
2f. Liu L., McKee M., Postema M. H. D.: Curr. Org. Chem. 2001, 5, 1133. <https://doi.org/10.2174/1385272013374699>
2g. Dondoni A., Marra A.: Chem. Rev. 2004, 104, 2557. <https://doi.org/10.1021/cr020079l>
2h. Postema M. H. D., Piper J. L., Betts R. L.: Synlett 2005, 1345. <https://doi.org/10.1055/s-2005-868500>
3. Goekjian P. G., Wei A., Kishi Y. in: Carbohydrate-Based Drug Discovery (Ch.-H. Wong, Ed.), p. 305. Wiley–VCH, Weinheim 2003; and references herein.
4a. Jimenéz-Barbero J., Espinosa J. F., Asensio J. L., Cañada F. J., Poveda A.: Adv. Carbohydr. Chem. Biochem. 2000, 56, 235, and references herein. <https://doi.org/10.1016/S0065-2318(01)56006-0>
4b. Fernández-Alonso M. C., Cañada F. J., Solís D., Cheng X., Kumaran G., André S., Siebert H.-Ch., Mootoo D. R., Gabius H.-J., Jiménez-Barbero J.: Eur. J. Org. Chem. 2004, 1604. <https://doi.org/10.1002/ejoc.200300679>
4c. García-Aparicio V., Fernández-Alonso M. C., Angulo J., Asensio J. L., Cañada F. J., Jimenéz-Barbero J., Mootoo D. R., Cheng X.: Tetrahedron: Asymmetry 2005, 16, 519. <https://doi.org/10.1016/j.tetasy.2004.11.072>
5a. Štěpánek P., Kniežo L., Dvořáková H., Vojtíšek P.: Synlett 2003, 963.
5b. Štěpánek P., Vích O., Kniežo L., Dvořáková H., Vojtíšek P.: Tetrahedron: Asymmetry 2004, 15, 1033. <https://doi.org/10.1016/j.tetasy.2004.01.023>
6. Wang Y., Goekjian P. G., Ryckman D. V., Kishi Y.: J. Org. Chem. 1988, 53, 4151. <https://doi.org/10.1021/jo00252a065>
7. Ferritto R., Vogel P.: Tetrahedron: Asymmetry 1994, 11, 2077. <https://doi.org/10.1016/S0957-4166(00)86285-0>
8. Pasquarello C., Picasso S., Demange R., Malissard M., Berger E. G., Vogel P.: J. Org. Chem. 2000, 65, 4251. <https://doi.org/10.1021/jo991952u>
9a. IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN): Symbols for Specifying the Conformation of Polysaccharide Chains. Recommendations 1981. Eur. J. Biochem. 1983, 131, 5.
9b. IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN): Symbols for Specifying the Conformation of Polysaccharide Chains. Recommendations 1981. Pure Appl. Chem. 1983, 55, 1269.
10. MM3(1996), Version of January 17, 1996, QCPE Program Number 698. Department of Chemistry, Indiana University, 800 East Kirkwood Ave., Bloomington, IN 47405-7102, U.S.A.
11a. Allinger N. L., Yuh Y. H., Lii J.-H.: J. Am. Chem. Soc. 1989, 111, 8551. <https://doi.org/10.1021/ja00205a001>
11b. Lii J.-H., Allinger N. L.: J. Am. Chem. Soc. 1989, 111, 8566. <https://doi.org/10.1021/ja00205a002>
11c. Allinger N. L., Rahman M., Lii J.-H.: J. Am. Chem. Soc. 1990, 112, 8293. <https://doi.org/10.1021/ja00179a012>
11d. Allinger N. L.: J. Am. Chem. Soc. 1977, 99, 8127. <https://doi.org/10.1021/ja00467a001>
12a. French A. D., Brady J. W.: ACS Symp. Ser. 1990, 430, 1. <https://doi.org/10.1021/bk-1990-0430.ch001>
12b. Pérez S., Imberty A., Engelsen S. B., Gruza J., Mazeau K., Jimenéz-Barbero J., Poveda A., Espinosa J. F., Van Eyck B. P., Johnson G., French A. D., Kouwijzer M. L., Grootenuis P. D. J., Bernardi A., Raimondi L., Senderowitz H., Durier V., Vergoten G., Rasmussen K.: Carbohydr. Res. 1998, 314, 141. <https://doi.org/10.1016/S0008-6215(98)00305-X>
13a. Van Alsenoy C., French A. D., Cao M., Newton S. Q., Schäfer L.: J. Am. Chem. Soc. 1994, 116, 9590. <https://doi.org/10.1021/ja00100a025>
13b. Rockwell G. P., Grindley T. B.: J. Am. Chem. Soc. 1998, 120, 10953. <https://doi.org/10.1021/ja981958l>
14. Karplus M.: J. Chem. Phys. 1959, 30, 11. <https://doi.org/10.1063/1.1729860>
15. Haasnoot C. A. G., De Leuw F. A. A. M., Altona C.: Tetrahedron 1980, 36, 2783. <https://doi.org/10.1016/0040-4020(80)80155-4>
16. Mikros E., Labrinidis G., Pérez S.: J. Carbohydr. Chem. 2000, 19, 1319. <https://doi.org/10.1080/07328300008544154>