Synthesis of phosphorylated derivatives of sucrose: 6,6′-di- phosphonate, 6- and 6′-phosphonates, and 6,6′-di-phosphine

Journal of Carbohydrate Chemistry

Volumn 29, Issue 7, 2010, Pages 332-347

  Gaweł, Anna ^a   Jarosz, Sławomir ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

Sucrose; Sucrose phosphines; Sucrose phosphonates

Indexed keywords

EID: 78650311636     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1080/07328303.2010.524958     Document Type: Article

References (31)

1. See for example: Khan, R. The chemistry of sucrose. Adv. Carbohydr. Chem. Biochem. 1976, 33, 235-294;
2. Hough, L. Selective substitution of hydroxyl groups in sucrose. In Sucrochemistry; ACS Symposium Series; Hickson, J. L., Ed.; ACS: Washington DC, 1977; vol. 41, 9-21;
3. Khan, R. Chemistry and new uses of sucrose: how important? Pure App. Chem. 1984, 56, 833-844;
4. Lichtenthaler, F. W. Carbohydrates as Organic Raw Materials, VCH: Weinheim, 1991; Vol. 1.;
5. Descotes, G. Carbohydrates as Organic Raw Materials, VCH: Weinheim, 1993; Vol. 2;
6. Mathlouthi, M.; Reiser, P. Sucrose: Properties and Applications; Blackie: Glasgow, 1995;
7. Immel, S.; Lichtenthaler, F. W. Molecular modeling of saccharides, 7. The conformation of sucrose in water: a molecular dynamics approach. Liebigs Ann. Chem. 1995, 11, 1925-1937;
8. Queneau, Y.; Fitremann, J.; Trombotto, S. The chemistry of unprotected sucrose: the selectivity issue. C. R. Chimie 2004, 7, 177-188.
9. Mach, M.; Jarosz, S.; Listkowski, A. Crown ether analogs from sucrose. J. Carbohydr. Chem. 2001, 20, 485-493; (Pubitemid 33389985)
10. Review: Jarosz, S.; Mach, M. Regio-and stereoselective transformations of sucrose at the terminal positions. Eur. J. Org. Chem. 2002, 769-780.
11. Queneau, Y.; Jarosz, S.; Lewandowski, B.; Fitremann, J. Sucrose chemistry and applications of sucrochemicals. Adv. Carbohydr. Chem. Biochem. 2007, 61, 217-292 and references therein.
12. Purves, C. B.; Hudson, C. S. The analysis of gamma-methylfructoside mixtures by means of invertase. IV. Behavior of sucrose in methyl alcohol containing hydrogen chlo-ride. J. Am. Chem. Soc., 1934, 56, 1973.
13. Hough, L.; Mufti, K. S.; Khan, R. Sucrochemistry: Part II. 6.6′-Di-O-tritylsucrose. Carbohydr. Res. 1972, 21, 144-147.
14. Franke, F.; Guthrie, R. D. t-Butyldimethylsilyl ethers of sucrose. Austr. J. Chem. 1977, 30, 639-647;
15. Franke, F.; Guthrie, R. D. 6, 6′-Di-O-t-butyldimethylsilylsucrose: studies on the re-arrangements accompanying deblocking of such silyl ethers. Austr. J. Chem. 1978, 31, 1285-1290.
16. Karl, H.; Lee, C. K.; Khan, R. Synthesis and reactions of tert-butyldiphenylsilyl ethers of sucrose. Carbohydr. Res. 1982, 101, 31-38.
17. Jarosz, S.; Listkowski, A.; Lewandowski, B.; Ciunik, Z.; Brzuszkiewicz, A. Macro-cyclic receptors containing sucrose skeleton. Tetrahedron 2005, 61, 8485-8492;
18. Jarosz, S.; Lewandowski, B. Synthesis and complexation properties towards the ammonium cation of aza-coronand analogues containing sucrose. Carbohydr. Res. 2008, 343, 965-969.
19. Lewandowski, B.; Jarosz, S. Chiral recognition of α- phenylethylamine by sucrose-based macrocyclic receptors. Chem. Commun. 2008, 6399-6401.
20. Jarosz, S.; Listkowski, A. Synthesis of macrocyclic derivatives containing sucrose unit. J. Carbohydr. Chem. 2003, 22, 753-763.
21. Jarosz, S.; Lewandowski, B.; Listkowski, A. Sucrose analogs containing sulfur functionalities. Phosphorus Silicon Sulfur 2009, 184, 1285-1295.
22. See for example: Dieguez, M.; Pamies, O.; Claver, C. Ligands derived from carbo-hydrates for asymmetric catalysis. Chem. Rev. 2004, 104, 3189-3215.
23. Scherrmann, M. C.; Boutboul, A.; Estramareix, B.; Hoffmann, A. S.; Lubineau, A. Binding properties and esterase activity of monoclonal antibodies elicited against su-crose 6-heptylphosphonate. Carbohydr. Res. 2001, 334, 295-307.
24. Jarosz, S.; Listkowski, A. Towards C-2 symmetrical macrocycles with incorporated sucrose unit. Can. J. Chem. 2006, 84, 492-496.
25. Ashby, E. C.; Gurumurthy, R.; Ridlehuber, R. W. Investigation of the purity of al-kali metal diphenylphosphides and their reactions with organic halides. Evidence for single electron transfer. J. Org. Chem. 1993, 58, 5832-5837.
26. Payne, N. C.; Stephan, D. W. Preparation and 31P nuclear magnetic resonance stud-ies of chiral phosphines. Can. J. Chem. 1980, 58, 15-21.
27. Otake, T. Studies of Tritylated Sucrose. I. Mono-O-tritylsucroses. Bull. Chem. Soc. Jpn. 1970, 43, 3199-3205;
28. Otake, T. Studies on Tritylated Sucrose. II. Di-O-Tritylsucroses., 1972, 45, 2895-2898;
29. Hough, L.; Mufti, K. S.; Khan, R. Sucrochemistry: Part II. 6.6′-Di-O-tritylsucrose. Carbohydr. Res., 1972, 21, 144-147.
30. Jarosz, S.; Mach, M.; Frelek, J. Synthesis and structural analysis of the higher analogs of sucrose. J. Carbohydr. Chem. 2000, 19, 693-715;
31. Mach, M.; Jarosz, S. Re-action of sugar phosphonates with sucrose aldehydes. Synthesis of higher analogs of sucrose. J. Carbohydr. Chem. 2001, 20, 411-424.