Skip to main content
SpringerLink
Log in

The approach to the synthesis of novel amino-C-glycosides

  • Research Article
  • Published:
Frontiers of Chemistry in China

Abstract

Stereoselective 1,3-dipolar cycloadditions of exo-glycals 1 to nitrones 2, 5 and 8 were investigated under the catalysis of Lewis acid or in a refluxing benzene or toluene solution, and afforded the corresponding cycloadducts of ketosyl spiro-isoxazolidines. The reductive cleavage of the N-O bond in the isoxazolidine ring and debenzylation by the catalytic hydrogenation [Pd(OH)2/C] were approached using the glucose-type cycloadducts 6b and 6e to alkyl-C-glycoside derivatives 12, providing a new access to a novel alkyl-C-glycoside containing an amino group on the side alkyl chain.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Levy D.E. and Tang C., The Chemistry of C-Glycosides, Elsevier Science Ltd., Oxford, 1995

    Google Scholar 

  2. Györgydeák Z. and Pelyvás I.F., C-Glycosylation, in Glycoscience: Chemistry and Chemical Biology, Eds. Fraser-Reid B.O., Tatsuta K. and Thiem J., Springer, Berlin, 2001, pp. 691–747

    Google Scholar 

  3. Boons G.J. Carbohydrate Chemistry, Blackie Academic and Professional, London, 1998, pp. 399–408

    Google Scholar 

  4. Somsak L., Carbanionic Reactivity of the Anomeric Center in Carbohydrates, Chem. Rev., 2001, 101: 81–135

    Article  CAS  Google Scholar 

  5. Du Y. and Linhardt R.J., Recent advances in stereoselective C-glycoside synthesis, Tetrahedron, 1998, 54: 9913–9959

    Article  CAS  Google Scholar 

  6. Dondoni A. and Marra A., Methods for Anomeric Carbon-Linked and Fused Sugar Amino Acid Synthesis: The Gateway to Artificial Glycopeptides, Chem. Rev., 2000, 100: 4395–4421

    Article  CAS  Google Scholar 

  7. Liu L., McKee M.M. and Postema H.D., Synthesis of C-Saccharides and Higher Congeners, Curr. Org. Chem., 2001, 5: 1133–1167

    Article  CAS  Google Scholar 

  8. Jarosz S. and Zamojski A., Carbohydrate Derivatives Containing the Carbon-Lithium and Carbon-Tin Bonds, Curr. Org. Chem., 2003, 7: 13–33

    Article  CAS  Google Scholar 

  9. Gallos J.K. and Koumbis A.E., 1,3-Dipolar Cycloadditions in the Synthesis of Carbohydrate Mimics. Part 1: Nitrile Oxides and Nitronates, Curr. Org. Chem., 2003, 7: 397–426

    Article  CAS  Google Scholar 

  10. Koumbis A.E. and Gallos J.K., 1,3-Dipolar Cycloadditions in the Synthesis of Carbohydrate Mimics. Part 2: Nitrones and Oximes, Curr. Org. Chem., 2003, 7: 585–628

    Article  CAS  Google Scholar 

  11. Koumbis A.E. and Gallos J.K., 1,3-Dipolar Cycloadditions in the Synthesis of Carbohydrate Mimics. Part 3: Azides, Diazo Compounds and Other Dipoles, Curr. Org. Chem., 2003, 7: 771–797

    Article  CAS  Google Scholar 

  12. Sharma G.V. M. and Krishna P.R., Carbohydrates: From ‘Chirons’ to New Glycosubstances, Curr. Org. Chem., 2004, 8: 1187–1209

    Article  CAS  Google Scholar 

  13. Abe H., Shuto S. and Matsuda A., Synthesis of the C-glycosidic analog of adenophostin A, a potent IP3 receptor agonist, using a temporary silicon-tethered radical coupling reaction as the key step, Tetrahedron Lett., 2000, 41: 2391–2394

    Article  CAS  Google Scholar 

  14. Godage H.Y. and Fairbanks A.J., Stereoselective synthesis of C-glycosides via Tebbe methylenation and Claisen rearrangement, Tetrahedron Lett., 2000, 41: 7589–7593

    Article  CAS  Google Scholar 

  15. Chiara J.L. and Sesmilo E., Samarium Diiodide-Mediated Reductive Coupling of Epoxides and Carbonyl Compounds: A Stereocontrolled Synthesis of C-Glycosides from 1,2-Anhydro Sugars, Angew. Chem. Int. Ed., 2002, 41: 3242–3246

    Article  CAS  Google Scholar 

  16. Roy R. and Das S.K., Recent applications of olefin metathesis and related reactions in carbohydrate chemistry, Chem. Commun., 2000, 519–529

  17. Paterson D.E., Griffin F.K., Alcaraz M.L. and Taylor R.J.K., A Ramberg-Bäcklund Approach to the Synthesis of C-Glycosides, C-Linked Disaccharides, and C-Glycosyl Amino Acids, Eur. J. Org. Chem., 2002, 1323–1336

  18. Sato S., Kumazawa T., Watanabe K., Matsuba S. and Onodera J., Conversion of diacetyl-C-(-D-glucopyranosyl) phloroglucinol to spiroketal compounds, Carbohydr. Res., 2004, 339: 429–433

    Article  CAS  Google Scholar 

  19. Potuzak J.S. and Tan D.S., Synthesis of Cl-alkyl-and acylglycals from glycals using a B-alkyl Suzuki-Miyaura cross coupling approach, Tetrahedron Lett. 2004, 45: 1797–1801

    Article  CAS  Google Scholar 

  20. Gómez A.M., Pedregosa A., Valverde S. and López J.C., Stereoselective synthesis of substituted exo-glycals from 1-exo-methylene pyranoses, Tetrahedron Lett., 2003, 44: 6111–6116

    Article  CAS  Google Scholar 

  21. Osborn H.M.I., Gemmell N. and Harwood L.M., 1,3-Dipolar cycloaddition reactions of carbohydrate derived nitrones and oximes, J. Chem. Soc., Perkin Trans. 1, 2002: 2419–2438

    Article  CAS  Google Scholar 

  22. Johson C.R. and Johons B.A., Suzuki Cross-Coupling of Carbohydrates: Synthesis of-Arylmethyl-C-glycosides and Aryl-Scaffolded Trisaccharide Mimics, Synlett, 1997, 1406–1408

  23. Cipolla L., Nicotra F., Vismara E. and Guerrini M., Synthesis of Stable Analogues of Glyceroglycolipids, Tetrahedron, 1997, 53: 6163–6170

    Article  CAS  Google Scholar 

  24. Vidal T., Haudrechy A. and Langois Y., Claisen-Ireland rearrangement: a new route to C-glycosides, Tetrahedron Lett., 1999, 40: 5677–5670

    Article  CAS  Google Scholar 

  25. Taillefumier C. and Chapleur Y., Synthesis and Uses of exo-Glycals, Chem. Rev., 2004, 104: 263–292

    Article  CAS  Google Scholar 

  26. Lin C.H., Lin H.C. and Yang W.B., exo-Glycal Chemistry: General Aspects and Synthetic Applications for Biochemical Use, Curr. Top. Med. Chem., 2005, 5: 1431

    Article  CAS  Google Scholar 

  27. Campbell A.D., Paterson D.E., Raynham T. M. and Taylor R. J. K., exo-Glycal approaches to C-linked glycosyl amino acid synthesis, Chem. Commun., 1999, 1599–1600

  28. Nishikawa T., Ishikawa M., Wada K. and Isobe M., Total Synthesis of α-C-Mannosyltryptophan, a Naturally Occurring C-Glycosyl Amino Acid, Synlett, 2001, 945–947

  29. Bartolozzi A., Capozzi G., Falciani C., Menichetti S., Nativi C. and Bacialli A. P., Regio-and Stereoselective Synthesis of 4′-Thiaspiracetals from Carbohydrates, J. Org. Chem., 1999, 64: 6490–6494

    Article  CAS  Google Scholar 

  30. Li X.L., Ohtake H., Takahashi H. and Ikegami S., An efficient synthesis of new 1′-C-methyl-O-D-disaccharides using 1-methylenesugars as the glycosyl donors, Tetrahedron, 2001, 57: 4283–4295

    Article  CAS  Google Scholar 

  31. Li X.L., Ohtake H., Takahashi H. and Ikegami S., A facile synthesis of 1′-C-alkyl-disaccharides from 1-C-alkyl-hexopyranoxes and methyl-1-C-alky-hexopyranosides, Tetrahedron, 2001, 57: 4297–4309

    Article  CAS  Google Scholar 

  32. Li X.L., Takahashi H., Ohtake H., Shiro M. and Ikegami S., Stereoselective synthesis and structure elucidation of spiro-ketodisaccharides, Tetrahedron, 2001, 57: 8053–8066

    Article  CAS  Google Scholar 

  33. Csuk R. and Glanzer R.I., Methylenation of Aldonolactones, Tetrahetron, 1991, 47: 1655–1664

    Article  CAS  Google Scholar 

  34. Li X.L., Takahashi H., Ohtake H. and Ikegami S., Synthesis of ketosyl spiro-isoxazolin dine by 1,3-dipolar cycloaddition of 1-methylenesugars with nitrones — a new access to C-glycosyl amino acids, Heterocycles, 2003, 59: 547–571

    Article  CAS  Google Scholar 

  35. Li X.L., Takahashi H., Ohtake H. and Ikegami S., 1,3-Dipolar cycloaddition of exo-methylenesugars with nitrone: approach to new amino-C-ketosyl disaccharides, Tetrahedron Lett., 2004, 45: 4123–4126

    Article  CAS  Google Scholar 

  36. Gothelf K.V. and Jorgensen K.A., Catalytic enantioselective 1,3-dipolar cycloaddition reactions of nitrones, Chem. Commun., 2000, 1449–1458

  37. Merino P., Frabco S., Graces N., Merchan F.L. and Tejero T., Modified nucleosides from nitrones: a new and efficient stereoselective approach to isoxazolidinyl thymidine derivatives, Chem. Commun., 1998, 493

  38. Merino P., Franco S., Merchan F.L. and Tejero T., Stereodivergent Approaches to the Synthesis of Isoxazolidine Analogues of r-Amino Acid Nucleosides. Total Synthesis of Isoxazolidinyl Deoxypolyoxin C and Uracil Polyoxin C, J. Org. Chem., 2000, 65: 5575–5589

    Article  CAS  Google Scholar 

  39. Bayon P., March P., Figueredo M. and Font J., Ti(IV) Promoted 1,3-Dipolar Cycloaddition of Nitrones to Vinyl Ethers, Tetrahedron, 1998, 54: 15691–15700

    Article  CAS  Google Scholar 

  40. Nicotra F., Russo G., Ronchetti F. and Toma L., Stereospecific synthesis of ethyl (2-acetamido-2-deoxy-α-D-glucopyranosyl)-acetate, Carbohydr. Res., 1983, 124: C5–C7

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. School of Chemistry and Environmental Sciences, Hebei University, Baoding, 071002, China

    Li Zhiwei, Li Xiaoliu, Duan Kefang & Chen Hua

Authors
  1. Li Zhiwei
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Li Xiaoliu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Duan Kefang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Chen Hua
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Li Xiaoliu.

About this article

Cite this article

Li, Z., Li, X., Duan, K. et al. The approach to the synthesis of novel amino-C-glycosides. Front. Chem. China 1, 281–286 (2006). https://doi.org/10.1007/s11458-006-0040-y

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11458-006-0040-y

Keywords

Search

Navigation