Modified one-pot protocol for the preparation of thioglycosides from unprotected aldoses via S-glycosyl isothiouronium salts

Journal of Carbohydrate Chemistry

Volumn 24, Issue 7, 2005, Pages 723-732

  Tiwari, Pallavi ^a   Agnihotri, Geetanjali ^a   Misra, Anup Kumar ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Acetylation; Aldoses; BF 3 OEt2; One pot; Stoichiometric; Thioglycosides; Thiourea

Indexed keywords

EID: 27844491198     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1080/07328300500256775     Document Type: Article

References (39)

1. Dwek, R.A. Glycobiology: towards understanding the function of sugar. Chem. Rev. 1996, 96, 683-720.
2. Bertozzi, C.R.; Kiessling, L.L. Chemical glycobiology. Science 2001, 291, 2357-2364.
3. Ritchie, G.E.; Moffatt, B.E.; Sim, R.B.; Morgan, B.P.; Dwek, R.A.; Rudd, P.M. Glycosylation and the complement system. Chem. Rev. 2002, 102, 305-320.
4. Varki, A. Biological roles of oligosaccharides: all of the theories are correct. Glycobiology 1993, 3, 97-130.
5. Parsiegla, G.; Reverbel-Leroy, C.; Tardif, C.; Belaich, J.P.; Driguez, H.; Haser, R. Crystal structures of the cellulase cel48f in complex with inhibitors and substrates give insights into its processive action. Biochemistry 2000, 39, 11238-11246.
6. Sulzenbacher, G.; Driguez, H.; Henrissat, B.; Schülein, M.; Davies, G.J. Structure of the Fusarium oxysporum endoglucanase I with a nonhydrolyzable substrate analogue: substrate distortion gives rise to the preferred axial orientation for the leaving group. Biochemistry 1996, 35, 15280-15287.
7. Czjzek, M.; Cicek, M.; Zamboni, V.; Burmeister, W.P.; Bevan, D.R.; Henrissat, B.; Esen, A. Crystal structure of a monocotyledon (maize ZMGlu1) β-glucosidase and a model of its complex with p-nitrophenyl β-D-thioglucoside. Biochem. J. 2001, 354, 37-46.
8. Comber, R.N.; Friedrich, J.D.; Dunshee, D.A.; Petty, S.L.; Secrist III, J.A. α-(1 → 2)-, α-(1 → 3)- and α-(1 → 6)-Linked thioglycosidic disaccharides: syntheses and anti-HIV testing of thiokojibiose octaacetate, thionigerose and thioisomaltose. Carbohydr. Res. 1994, 262, 245-255.
9. Kiefel, M.J.; Beisner, B.; Bennett, S.; Holmes, I.D.; von Itzstein, M. Synthesis and biological evaluation of n-acetylneuraminic acid-based rotavirus inhibitors. J. Med. Chem. 1996, 39, 1314-1320.
10. Eisele, T.; Toepfer, A.; Kretzschmar, G.; Schmidt, R.R. Synthesis of a thio-linked analogue of sialyl Lewis X. Tetrahedron Lett. 1996, 37, 1389-1392.
11. Toshima, K.; Tatsuta, K. Recent progress in O-glycosylation methods and its application to natural products synthesis. Chem. Rev. 1993, 93, 1503-1531.
12. Fukase, K.; Hasuoka, A.; Kinoshita, I.; Aoki, Y.; Kusumoto, S. A stereoselective glycosidation using thioglycosides, activation by combination of N-bromosuccinimide and strong acid salts. Tetrahedron 1995, 51, 4923-4932.
13. Garegg, P.J. Thioglycosides as glycosyl donors in oligosaccharide synthesis. Adv. Carbohydr. Chem. Biochem. 1997, 52, 179-205.
14. Hasegawa, A.; Kiso, M. Systematic synthesis of gangliosides towards the elucidation and biomedical application of their biological functions. In Carbohydrates, Synthetic methods and Applications in Medicinal Chemistry; Ogura, H., Hasegawa, A., Suami, T., Eds.; 1992, 243-266.
15. Das, S.K.; Roy, N. An improved method for the preparation of some ethyl 1-thioglycosides. Carbohydr. Res. 1996, 296, 275-277.
16. Olsson, L.; Kelberlau, S.; Jia, Z.J.; Fraser-Reid, B. Access to tetrachlorphthalimide-protected ethyl 2-amino-2-deoxy-1-thio-β-D- glucopyranosides. Carbohydr. Res. 1998, 314, 273-276.
17. Matsui, H.; Furukawa, J.; Awano, T.; Nishi, N.; Sakairi, N. Lauryl and stearyl thioglycosides: preparation and reactivity of the glycosyl donor. Chem. Lett. 2000, 326-327.
18. Pozsgay, V.; Jennings, H.J. A new, stereoselective synthesis of methyl 1,2-trans-1-thioglycosides. Tetrahedron Lett. 1987, 28, 1375-1376.
19. Nambiar, S.; Daeuble, J.F.; Doyle, R.J.; Taylor, K.G. Facile synthesis of silylated thioglycosides. Tetrahedron Lett. 1989, 30, 2179-2182.
20. Agnihotri, G.; Tiwari, P.; Misra, A.K. One-pot synthesis of per-O-acetylated thioglycosides from unprotected reducing sugars. Carbohydr. Res. 2005, 340, 1393-1396.
21. Dohi, H.; Nishida, Y.; Tanaka, H.; Kobayashi, K. O-methoxycarbonylphenyl- 1-thio-β-D-galactopyranoside, a non-malodorous thioglycosylation donor for the synthesis of globosyl α-(1-4)-linkages. Synlett 2001, 1446-1448.
22. Dohi, H.; Nishida, Y.; Takeda, T.; Kobayashi, K. Convenient use of non-malodorous thioglycosylation donors for the synthesis of multivalent globo- and iso-globosyl trisaccharides. Carbohydr. Res. 2002, 337, 983-989.
23. Chipowsky, S.; Yuan, C.L. Synthesis of 1-thioaldosides having an amino group at the aglycon terminal. Carbohydr. Res. 1973, 31, 339-346.
24. Driguez, H.; Szeja, W. Facile synthesis of 1,2-trans-nitrophenyl-1- thioglycopyranosides. Synthesis 1994, 1413-1414.
25. García-López, J.J.; Hernández-Mateo, F.; Isac-García, J.; Kim, J.M.; Roy, R.; Santoyo-González, F.; Vargas-Berenguel, A. Synthesis of per-glycosylated β-cyclodextrins having enhanced lectin binding affinity. J. Org. Chem. 1999, 64, 522-531.
26. Gan, Z.; Roy, R. Transition metal-catalyzed syntheses of 'rod-like' thioglycoside dimmers. Tetrahedron Lett. 2000, 41, 1155-1158.
27. Ibatullin, F.M.; Selivanov, S.I.; Shavva, A.G. A general procedure for conversion of S-glycosyl isothiourea derivatives into thioglycosides, thiooligosaccharides and glycosyl thioesters. Synthesis 2001, 419-422.
28. Ibatullin, F.M.; Shabalin, K.A.; Jänis, J.V.; Selivanov, S.I. Stereoselective synthesis of thioxylooligosaccharides from S-glycosyl isothiourea precursors. Tetrahedron Lett. 2001, 42, 4565-4567.
29. Ibatullin, F.M.; Shabalin, K.A.; Jänis, J.V.; Shavva, A.G. Reaction of 1,2-transglycosyl acetates with thiourea: a new entry to 1-thiosugars. Tetrahedron Lett. 2003, 44, 7961-7964.
30. Pakulski, Z.; Pierozynski, D.; Zamojski, A. Reaction of sugar thiocyanates with Grignard reagents. New synthesis of thioglycosides. Tetrahedron 1994, 50, 2975-2992.
31. Karrer, P.; Rosa, B.; Günther, S.; Harder, W.; Lang, L. Zur Kenntnis der Glucoside IX. Helv. Chim. Acta 1921, 4, 130-148.
32. Crich, D.; Mataka, J.; Zakharov, L.N.; Rheingold, A.L.; Wink, D.J. Stereoselective formation of glycosyl sulfoxides and their subsequent equilibration: ring inversion of an α-xylopyranosyl sulfoxide dependent on the configuration at sulfur. J. Am. Chem. Soc. 2002, 124, 6028-6036.
33. Ziegler, T.; Dettmann, R.; Duszenko, M.; Kolb, V. Synthesis of octyl O- and S-glycosides related to the GPI anchor of Trypanosoma brucei and their in vitro galactosylation by trypanosomal α-galactosyltransferases. Carbohydr. Res. 1996, 295, 7-24.
34. Durette, P.L.; Shen, T.Y. Insulin-like, and insulin-antagonistic, carbohydrate derivatives. The synthesis of aryl and aralkyl D-mannopyranosides and 1-thio-D-mannopyranosides. Carbohydr. Res. 1980, 81, 261-274.
35. Kartha, K.P.R.; Cura, P.; Aloui, M.; Readman, S.K.; Rutherford, T.J.; Field, R.A. Observations on the activation of methyl thioglycosides by iodine and its interhalogen compounds. Tetrahedron: Asymmetry 2000, 11, 581-594.
36. Saito, S.; Furumoto, T.; Ochiai, M.; Hosono, A.; Hoshino, H.; Haraguchi, U.; Ikeda, R.; Shimada, N. Synthetic studies on the relationship between anti-HIV activities and micelle forming abilities of various alkylated glycyrrhetinate diglycoside sodium sulfates and related compounds. Eur. J. Med. Chem. 1996, 31, 365-381.
37. 3: effective usage of the neighbouring group participation strategy. Carbohydr. Res. 1996, 284, 207-222.
38. Koto, S.; Yoshida, T.; Takenaka, K.; Zen, S. A through process for the preparation of methyl per-O-acetyl-1-thio-glycosides from aldoses. Bull. Chem. Soc. Jpn. 1982, 55, 3667-3668.
39. Chretien, F.; Cesare, P.D.; Gross, B. Synthesis of thiodisaccharides using phase-transfer catalysis. J. Chem. Soc. Perkin Trans. 1. 1988, 3297-3300.