Microwave irradiation for accelerating the synthesis of thioglycosides

Synthetic Communications

Volumn 36, Issue 19, 2006, Pages 2769-2785

  El Ashry, E S H ^a   Awad, L F ^a   Hamid, H M Abdel ^a   Atta, A I ^a  

^a Alexandria University Faculty Of Science   (Egypt)

Author keywords

Alkylating agents; Microwave irradiation; Pyridine; Quinoxaline; Thioglycosides

Indexed keywords

ALKYLATING AGENT; PYRIDINE; QUINOXALINE; THIOGLYCOSIDE; THIOGLYCOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; COMPARATIVE STUDY; MICROWAVE IRRADIATION; REACTION ANALYSIS; REACTION TIME; SYNTHESIS;

EID: 33750090689     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910600767314     Document Type: Article

References (47)

1. Defaye, J.; Gelas, J. In Studies in Natural Products Chemistry; Atta-ur-Rhman, Eds.; Elsevier: Amsterdam, 1991; Vol. 8E, p. 315.
2. Driguez, H. Thiooligosaccharides in glycobiology. Topics Curr. Chem. 1997, 187, 85.
3. Gil, V.; Macleod, A. J. Effects of a Lepidium sativum enzyme preparation on the degradation of glucosinolates. Phytochemistry 1980, 19, 2071.
4. (a) Horton, D.; Hutson, D. H. Developments in the chemistry of thio sugars. Adv. Carbohydr. Chem. 1963, 18, 123;
5. (b) Witczak, Z. J. Thio sugars: Biological relevance as potential new therapeutics. Curr. Med. Chem. 1999, 6, 165;
6. (c) Suzuki, Y.; Sato, K.; Kiso, M.; Hasegawa, A. Glycoconjugate 1990, 7, 349;
7. (d) Wilson, J. C.; Kiefel, M. J.; Angus, D. I.; Itzstein, M. V. Investigation of the stability of thiosialosides toward hydrolysis by sialidases using NMR spectroscopy. Org. Lett. 1999, 1, 443.
8. Taylor, C. M. Glycopeptides and glycoproteins: Focus on the glycosidic linkage. 1998, 54, 11317.
9. (a) El Ashry, E. S.H.; Rashed, N.; Shobier, A. H. Glycosidase inhibitors and their chemotherapeutic value, part 1. Pharmazie 2000, 55, 251;
10. (b) El Ashry, E. S.H.; Rashed, N.; Shobier, A. H. Glycosidase inhibitors and their chemotherapeutic value, part 2. Pharmazie 2000, 55, 331;
11. (c) El Ashry, E. S.H.; Rashed, N.; Shobier, A. H. Glycosidase inhibitors and their chemotherapeutic value, part 3. Pharmazie 2000, 55, 403;
12. (d) Witczak, Z. J.; Nieforth, K. A. Carbohydrates in Drug Design; Marcel Dekker: New York, 1997;
13. (e) Robina, I.; Vogel, P.; Witczak, Z. J. Synthesis and biological properties of monothiosaccharides. Curr. Org. Chem. 2001, 5, 1177;
14. (f ) Look, G. C.; Fotsch, C. H.; Wong, C. H. Acc. Chem. Res. 1993, 26, 182;
15. (g) Vasella, T. D.; Heightman, A. T. Angew. Chem. Int. Ed. 1999, 8E 315;
16. (h) Witczak, Z. J.; Sun, J.; Mielgu, J. Biorg. Med. Chem. Lett. 1995, 5, 2169;
17. (i) Witczak, Z. J.; Chabra, R.; Chen, H.; Xie, X.-Q. Thiosugars II. A novel approach to thiodisaccharides: The synthesis of 3-deoxy-4-thiocellobiose from levoglucosenone. Carbohydr. Res. 1997, 301, 167.
18. (a) Rho, D.; Desrochers, M.; Jurasek, L.; Driguez, H.; Defaye, J. J. Bacteriol. 1982, 149, 47;
19. (b) Defaye, J.; Guillot, M.; Biely, P.; Vrsanska, M. Positional isomers of thioxylobiose, their synthesis and inducing ability for D-xylan-degrading enzymes in the yeast Cryptococcus albidus. Carbohydr. Res. 1992, 228, 47;
20. (c) Brik, R.; Ikan, A.; Bravdo, B.; Braun, S.; Shoseyov, O. Appl. Biochem. Biotechnol. 1997, 66, 25;
21. (d) Alhadeff, J. A.; Miller, A. L.; O'Brien, J. S. Purification of human placental α-L-fucosidase by affinity chromatography. Anal. Biochem. 1974, 60, 424;
22. (e) Schnar, R. L.; Lee, Y. C. Polyacrylamide gels copolymerized with active esters: A new medium for affinity systems? Biochemistry 1975, 14, 1535;
23. (f) Orgerat, C.; Seillier, E.; Gautier, C.; Defaye, J.; Driguez, H. 4-Thiocellooligosaccharides: Their synthesis and use as ligands for the separation of cellobiohydrolases of Trichoderma reesei by affinity chromatography. Carbohydr. Res. 1992, 224, 29.
24. Alexei, V.; Demchenko, N. M.; Cristina, D. M. S-Benzoxazolyl (SBox) glycosides as novel, versatile glycosyl donors for stereoselective 1,2-cis glycosylation. Org. Lett. 2003, 5, 455.
25. Peter, F.; Per, J.; Stefon, O.; Gunnar, R.; Silwanis, B. Glycosyl 1-piperidinecarbodithioates in the synthesis of glycosides. Carbohydrate Res. 1991, 211, 157.
26. Koich, F.; Atsush, H.; Ikuko, K.; Ytaka, A.; Shoicki, K. A stereoselective glycosidation using thioglycosides, activation by combination of N-bromosuccinimide and strong acid salts. Tetrahedron 1995, 51, 4923.
27. Geert-Jan, B.; Richard, G.; Duncan, H. Chemoselective glycosylations (part 1): Differences in size of anomeric leaving groups can be exploited in chemoselective glycosylations. Tetrahedron Lett. 1995, 6325.
28. (a) Matta, K. L.; Girotra, R. N.; Barlow, J. J. Synthesis of p-nitrobenzyl and p-nitrophenyl 1-thioglycopyranosides. Carbohydr. Res. 1975, 101, 43;
29. (b) Tsvetkov, Y. E.; Byramova, N. E.; Backinovsky, L. V. A simple preparation of aromatic 1-thioglycosides. Carbohydr. Res. 1983, 115, 254.
30. Lemieux, R. U.; Shyluk, W. P. A new synthesis of β-glucopyranosides. Can. J. Chem. 1953, 31, 528.
31. (a) Schmidt, R. R.; Stumpp, M. Synthese von 1-thioglycosiden. Liebigs Ann. Chem. 1983, 1249;
32. (b) Andrews, J. S.; Pinto, B. M. Synthesis of thio analogue of n-propyl kojibioside, a potential glucosidase inhibitor. Carbohydr. Res. 1995, 270, 51;
33. a) epitope. Carbohydr. Res. 1998, 306, 81.
34. Li, Z. J.; Liu, P.-L.; Li, Z.-J.; Qiu, D.-X.; Gai, M.-S. Studies on glycosides, VII: A highly stereoselective synthesis of 1-thioglycosides. Synth. Commun. 1990, 20, 2169.
35. Li, P.; Sun, L.; Landry, D. W.; Zhao, K. Synthesis of 1-thioglycosides. Carbohydr. Res. 1995, 275, 179.
36. Hugues, D.; Wieslaw, S. Facile synthesis of 1,2-trans-nitrophenyl-1- thioglycopyranosides. Synthesis 1994, 1413.
37. Ibatullin, F. M.; Selivanov, S. I.; Shovva, A. G. A general procedure for conversion of S-glycosyl isothiourea derivatives into thioglycosides, thiooligosaccharides and glycosyl thioesters. Synthesis 2001, 419.
38. El Ashry, E. S.H.; Awad, L. F.; Abdel Hamid, H. M.; Atta, A. I. Synthesis of interglycosidically S-linked 1-thio-oligosaccharides under microwave irradiation. EUROCARB12 Conference, Grenoble, France, 2003; PB 074, 286.
39. Leaback, D. H.; Walker, P. G. The preparation and properties of acetochloroglucosamine and its use in the synthesis of 2-acetamido-2-deoxy-D- glucoside (N-acetyl-β-D-glucosaminides). J. Chem. Soc. 1957, 4754.
40. Bonner, W. A.; Kahn, J. E. A study of some S-(polyacetyl-β-D- glycopyranosyl)-thiouronium halides. J. Am. Chem. Soc. 1951, 73, 2241.
41. (a) Horton, D.; Wolfrom, M. L.; Thiosugars, I.: Synthesis of derivatives of 2-amino-2-deoxy-1-thio-D-glucose. J. Org. Chem. 1962, 27, 1794;
42. (b) Gerd, H.; Hindsgall, O. Solid-phase synthesis of thio- oligosaccharides. Angew. Chem. Int. Ed. 1999, 38, 1782.
43. Hutson, D. H. 6-S-β-D-Glucopyranosyl-6-thio-D-glucopyranose. A thioglucosidic analogue of gentiobiose. J. Chem. Soc. C 1967, 442.
44. Cerny, M.; Pacak, J. A new method for the preparation of acetylated β-D-thioglucopyranosides. Collection Czechoslov. Chem. Commun. 1959, 24, 2566.
45. Ogawa, S.; Rinehart, K. L.; Kimura, G.; Johnson, R. P. J. Org. Chem. 1974, 39, 812.
46. Matta, K. L.; Johnson, A. Z.; Girotora, R. N.; Barlow, J. J. Synthesis of 2-acetamido-2-deoxy-1-thio-β-D-glucopyranosides. Carbohydr. Res. 1973, 30, 414.
47. Wagner, G.; Frenzel, H. Über die syntheses von glucosiden von 2-hydroxy- und 2-mercapto-chinoxalinen. Arch. Pharm. 1967, 300, 433.