Crown ether analogs from sucrose

Journal of Carbohydrate Chemistry

Volumn 20, Issue 6, 2001, Pages 485-493

  Mach, Mateusz ^a   Jarosz, Slawomir ^a   Listkowski, Arkadiusz ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035537720     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1081/CAR-100106931     Document Type: Article

References (18)

1. Haines, A. H. Relative reactivities of hydroxyl groups in carbohydrates. Adv. Carbohydr. Chem. Biochem. 1976, 33, 11-109; Jarosz, S. The chemistry of sucrose. Polish J. Chem. 1996, 70, 972-987; see also: Carbohydrates as Organic Raw Materials, Lichtenthaler, F. W. Ed.; VCH Verlagsgesellschaft mbH, 1991.
2. Haines, A. H. Relative reactivities of hydroxyl groups in carbohydrates. Adv. Carbohydr. Chem. Biochem. 1976, 33, 11-109; Jarosz, S. The chemistry of sucrose. Polish J. Chem. 1996, 70, 972-987; see also: Carbohydrates as Organic Raw Materials, Lichtenthaler, F. W. Ed.; VCH Verlagsgesellschaft mbH, 1991.
3. Haines, A. H. Relative reactivities of hydroxyl groups in carbohydrates. Adv. Carbohydr. Chem. Biochem. 1976, 33, 11-109; Jarosz, S. The chemistry of sucrose. Polish J. Chem. 1996, 70, 972-987; see also: Carbohydrates as Organic Raw Materials, Lichtenthaler, F. W. Ed.; VCH Verlagsgesellschaft mbH, 1991.
4. Khan, R. Chemistry and new uses of sucrose: how important Pure Appl. Chem. 1984, 56, 833-844 and references therein.
5. Jarosz, S.; Mach, M.; Frelek, J. Synthesis and structural analysis of the higher analogs of sucrose. J. Carbohydr. Chem. 2000, 19, 693-715 and references therein.
6. Otake, T. Studies of tritylated sucrose. I. Mono-O-tritylsucroses. Bull. Chem. Soc. Jpn. 1970, 45, 3199-3205.
7. Hough, L.; Mufti, K. S.; Khan, R. Sucrochemistry. Part II. 6,6′-Di-O-tritylsucrose. Carbohydr. Res. 1972, 21, 144-147.
8. Jarosz, S. Selective reactions of the free hydroxyl groups of 2,3,4,3′,4′-penta-O-benzyl-sucrose. J. Carbohydr. Chem. 1996, 15, 73-79.
9. See for example: Laidler, D. L.; Stoddard, J. F. Chiral asymmetric crown ethers. Carbohydr. Res. 1977, 55, C1-C4; Hain, W.; Lehnert, R.; Röttele, H.; Schröder, G. Chirale Kronenether mit Monosachariden als Chiralitätsträgern. Tetrahedron Lett. 1978, 625-628; Haines, A. H.; Hodgkisson, I.; Smith, Ch. Benzo-15-crown-5 derivatives. Synthesis and properties as ion-extraction and ion-transport agents. J. Chem. Soc., Perkin Trans. 1 1983, 311-318; Pietraszkiewicz, M. Jurczak, J. Synthesis of chiral diaza-crown ethers incorporating carbohydrate units. Tetrahedron 1984, 40, 2967-2970; Vicent, C.; Jimenez-Barbero, J.; Martin-Lomas, M.; Penades, S.; Cano, F. X.; Foces-Foces, C. Structural studies of chiral receptors incorporating D-glucose. J. Chem. Soc., Perkin Trans. 2 1991, 905-912; Dumont-Hornebeck, B.; Joly, J.-L.; Coulon, J.; Chapleur, Y. Synthesis of di-and trisaccharides incorporating a crown ether macrocycle. Carbohydr. Res. 1999, 320, 147-160.
10. See for example: Laidler, D. L.; Stoddard, J. F. Chiral asymmetric crown ethers. Carbohydr. Res. 1977, 55, C1-C4; Hain, W.; Lehnert, R.; Röttele, H.; Schröder, G. Chirale Kronenether mit Monosachariden als Chiralitätsträgern. Tetrahedron Lett. 1978, 625-628; Haines, A. H.; Hodgkisson, I.; Smith, Ch. Benzo-15-crown-5 derivatives. Synthesis and properties as ion-extraction and ion-transport agents. J. Chem. Soc., Perkin Trans. 1 1983, 311-318; Pietraszkiewicz, M. Jurczak, J. Synthesis of chiral diaza-crown ethers incorporating carbohydrate units. Tetrahedron 1984, 40, 2967-2970; Vicent, C.; Jimenez-Barbero, J.; Martin-Lomas, M.; Penades, S.; Cano, F. X.; Foces-Foces, C. Structural studies of chiral receptors incorporating D-glucose. J. Chem. Soc., Perkin Trans. 2 1991, 905-912; Dumont-Hornebeck, B.; Joly, J.-L.; Coulon, J.; Chapleur, Y. Synthesis of di-and trisaccharides incorporating a crown ether macrocycle. Carbohydr. Res. 1999, 320, 147-160.
11. See for example: Laidler, D. L.; Stoddard, J. F. Chiral asymmetric crown ethers. Carbohydr. Res. 1977, 55, C1-C4; Hain, W.; Lehnert, R.; Röttele, H.; Schröder, G. Chirale Kronenether mit Monosachariden als Chiralitätsträgern. Tetrahedron Lett. 1978, 625-628; Haines, A. H.; Hodgkisson, I.; Smith, Ch. Benzo-15-crown-5 derivatives. Synthesis and properties as ion-extraction and ion-transport agents. J. Chem. Soc., Perkin Trans. 1 1983, 311-318; Pietraszkiewicz, M. Jurczak, J. Synthesis of chiral diaza-crown ethers incorporating carbohydrate units. Tetrahedron 1984, 40, 2967-2970; Vicent, C.; Jimenez-Barbero, J.; Martin-Lomas, M.; Penades, S.; Cano, F. X.; Foces-Foces, C. Structural studies of chiral receptors incorporating D-glucose. J. Chem. Soc., Perkin Trans. 2 1991, 905-912; Dumont-Hornebeck, B.; Joly, J.-L.; Coulon, J.; Chapleur, Y. Synthesis of di-and trisaccharides incorporating a crown ether macrocycle. Carbohydr. Res. 1999, 320, 147-160.
12. See for example: Laidler, D. L.; Stoddard, J. F. Chiral asymmetric crown ethers. Carbohydr. Res. 1977, 55, C1-C4; Hain, W.; Lehnert, R.; Röttele, H.; Schröder, G. Chirale Kronenether mit Monosachariden als Chiralitätsträgern. Tetrahedron Lett. 1978, 625-628; Haines, A. H.; Hodgkisson, I.; Smith, Ch. Benzo-15-crown-5 derivatives. Synthesis and properties as ion-extraction and ion-transport agents. J. Chem. Soc., Perkin Trans. 1 1983, 311-318; Pietraszkiewicz, M. Jurczak, J. Synthesis of chiral diaza-crown ethers incorporating carbohydrate units. Tetrahedron 1984, 40, 2967-2970; Vicent, C.; Jimenez-Barbero, J.; Martin-Lomas, M.; Penades, S.; Cano, F. X.; Foces-Foces, C. Structural studies of chiral receptors incorporating D-glucose. J. Chem. Soc., Perkin Trans. 2 1991, 905-912; Dumont-Hornebeck, B.; Joly, J.-L.; Coulon, J.; Chapleur, Y. Synthesis of di-and trisaccharides incorporating a crown ether macrocycle. Carbohydr. Res. 1999, 320, 147-160.
13. See for example: Laidler, D. L.; Stoddard, J. F. Chiral asymmetric crown ethers. Carbohydr. Res. 1977, 55, C1-C4; Hain, W.; Lehnert, R.; Röttele, H.; Schröder, G. Chirale Kronenether mit Monosachariden als Chiralitätsträgern. Tetrahedron Lett. 1978, 625-628; Haines, A. H.; Hodgkisson, I.; Smith, Ch. Benzo-15-crown-5 derivatives. Synthesis and properties as ion-extraction and ion-transport agents. J. Chem. Soc., Perkin Trans. 1 1983, 311-318; Pietraszkiewicz, M. Jurczak, J. Synthesis of chiral diaza-crown ethers incorporating carbohydrate units. Tetrahedron 1984, 40, 2967-2970; Vicent, C.; Jimenez-Barbero, J.; Martin-Lomas, M.; Penades, S.; Cano, F. X.; Foces-Foces, C. Structural studies of chiral receptors incorporating D-glucose. J. Chem. Soc., Perkin Trans. 2 1991, 905-912; Dumont-Hornebeck, B.; Joly, J.-L.; Coulon, J.; Chapleur, Y. Synthesis of di-and trisaccharides incorporating a crown ether macrocycle. Carbohydr. Res. 1999, 320, 147-160.
14. See for example: Laidler, D. L.; Stoddard, J. F. Chiral asymmetric crown ethers. Carbohydr. Res. 1977, 55, C1-C4; Hain, W.; Lehnert, R.; Röttele, H.; Schröder, G. Chirale Kronenether mit Monosachariden als Chiralitätsträgern. Tetrahedron Lett. 1978, 625-628; Haines, A. H.; Hodgkisson, I.; Smith, Ch. Benzo-15-crown-5 derivatives. Synthesis and properties as ion-extraction and ion-transport agents. J. Chem. Soc., Perkin Trans. 1 1983, 311-318; Pietraszkiewicz, M. Jurczak, J. Synthesis of chiral diaza-crown ethers incorporating carbohydrate units. Tetrahedron 1984, 40, 2967-2970; Vicent, C.; Jimenez-Barbero, J.; Martin-Lomas, M.; Penades, S.; Cano, F. X.; Foces-Foces, C. Structural studies of chiral receptors incorporating D-glucose. J. Chem. Soc., Perkin Trans. 2 1991, 905-912; Dumont-Hornebeck, B.; Joly, J.-L.; Coulon, J.; Chapleur, Y. Synthesis of di-and trisaccharides incorporating a crown ether macrocycle. Carbohydr. Res. 1999, 320, 147-160.
15. Otake, T. Studies of tritylsucrose. II. Di-O-tritylsucrose. Bull. Chem. Soc. Jpn. 1972, 45, 2895-2898.
16. The only compound with the secondary groups protected as benzyl ether was 6,6′-dideoxy-6,6′-diazido-1′,2,3,3′,4,4′-hexa-O-be nzylsucrose prepared by benzylation of 6,6′-dideoxy-6,6′-diazido-sucrose [Gradnig, G.; Legier, G.; Stuetz, A. E. A novel approach to 1-deoxynojirimycin system: synthesis from sucrose of 2-acetamido-1,2-dideoxy nojirimycin, as well as some 2-N-modified derivatives. Carbohydr. Res. 1996, 287, 49-57].
17. These ditosylates were obtained according to the literature methods: Ouchi, M.; Inoue, Y.; Liu, Y.; Nagamune, S.; Nakamura, S. Convenient and efficient tosylation of oligoethylene glycols and the related alcohols in tetrahydrofuran-water in the presence of sodium hydroxide. Bull. Chem. Soc. Jpn. 1990, 63, 1260-1262.
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