A novel oxidatively removable linker and its application to α-selective solid-phase oligosaccharide synthesis on a macroporous polystyrene support

Synlett

Volumn , Issue 7, 1999, Pages 1074-1078

  Fukase, Koichi ^a   Nakai, Yoshihiko ^a   Egusa, Kenji ^a   Porco Jr , John A ^a,b   Kusumoto, Shoichi ^a  

^a OSAKA UNIVERSITY   (Japan)

^b Argonaut Technologies   (United States)

Author keywords

Acylaminobenzyl linker; Glycosylation; Macroporous polystyrene; Solid phase synthesis; Thioglycoside

Indexed keywords

ARGOPORE; CARBOXYLIC ACID DERIVATIVE; CROSS LINKING REAGENT; DISACCHARIDE; ETHER; ETHER DERIVATIVE; GLYCOCONJUGATE; MONOSACCHARIDE; OLIGOSACCHARIDE; POLYMER; POLYSTYRENE DERIVATIVE; THIOGLYCOSIDE; TRISACCHARIDE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; GLYCOSYLATION; OXIDATION; SOLID; STRUCTURE ACTIVITY RELATION;

EID: 0032776027     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2779     Document Type: Article

References (37)

1. a) Danishefsky, S. J.; McClure, K. F.; Randolph, J. T.; Ruggeri, P. B. Science 1993, 260, 1307.
2. b) Randolph J. T.; Danishefsky, S. J. Angew. Chem. Int. Ed, Engl. 1994, 33, 1470.
3. c) Randolph, J. T.; McClure, K. F.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5712.
4. d) Zheng, C.; Seeberger, P. H.; Danishefsky, S. J. J. Org. Chem. 1998, 63, 1126.
5. a) Yan, L.; Taylor, C. M.; Goodnow Jr., R.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 6953.
6. b) Liang, R.; Yan, L.; Loebach, J.; Ge, M.; Uozumi, Y.; Sekanina, K.; Horan, N.; Gilderskeve, J.; Thompson, C.; Smith, A.; Biswas, K.; Still, W. C.; Kahne, D. Science 1996, 274, 1520.
7. a) Rademann, J.; Schmidt, R. R. Tetrahedron Lett. 1996, 37, 3989.
8. b) Rademann, J.; Schmidt, R. R. J. Org. Chem. 1997, 62, 3650.
9. c) Heckel, A.; Mross, E.; Jung, K.-H.; Rademann, J.; Schmidt, R. R. Synlett 1998, 171.
10. Nicolaou, K. C.; Winssinger, N.; Pastor, J.; DeRoose, F. J. Am. Chem. Soc. 1997, 119, 449.
11. Douglas, S. P.; Whitfield, D. M.; Krepinsky, J. J. J. Am. Chem. Soc. 1995, 117, 2116.
12. a) Ito, Y.; Kanie, O.; Ogawa, T. Angew. Chem. Int. Ed. Engl. 1996, 35, 2510.
13. b) Ito, Y.; Ogawa, T. J. Am. Chem. Soc. 1997, 119, 5562.
14. c) Kononov, L. O.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1997, 38, 1599.
15. a) Fukase, K.; Nakai, Y.; Kanoh, T.; Kusumoto, S. Synlett 1998, 85.
16. b) Fukase, K.; Kinoshita, I.; Kanoh, T.; Hasuoka, A.; Kusumoto, S. Tetrahedron 1996, 52, 3897.
17. c) Fukase, K.; Hasuoka, A.; Kinoshita, I.; Aoki, Y.; Kusumoto, S. Tetrahedron 1995, 51, 4923.
18. Commercially available from Argonaut Technologies, San Carlos, California: http://www.argotech.com. For investigations of other highly crosslinked macroporous resins, see: Hori, M.; Graven, D.J.; Wentworth, P., Jr.; Janda, K.D. Bioorganic Med. Chem. Lett. 1998, 8, 2363.
19. a) Kobayashi, S.; Tetrahedron Lett. 1998, 39
20. b) Hanessian, S.; Xie, F. Tetrahedron Lett. 1998, 39, 737.
21. c) Hanessian, S.; Xie, F. Tetrahedron Lett. 1998, 39, 733.
22. Fukase, K.; Egusa, K.; Nakai, Y.; Kusumoto, S. Molecular Diversity 1997, 2, 182.
23. +].
24. Fukase, K.; Matsumoto, T.; Ito, N.; Yoshimura, T.; Kotani, S.; Kusumoto, S. Bull. Chem, Soc. Jpn. 1992, 65, 2643.
25. 3 decomposes the p-nitrobenzyl group.
26. 3 decomposes the p-nitrobenzyl group.
27. Fukase, K.; Yoshimura, T.; Kotani, S.; Kusumoto, S. Bull. Chem. Soc. Jpn. 1994, 67, 473.
28. 2O in MeOH also gave 3 in good yields.
29. 2, and diethyl ether. Yield of the resin 1.68 g (Theoretical yield of the resin is 1.68 g.).
30. 4, and concentrated in vacuo. The residue was purified with preparative silica-gel TLC (toluene-EtOAc = 1:1) to give colorless solid. Yield 19.6 mg (91%).
31. 2 and ether. After Molecular Sieves 4Å beads were removed by picking with forceps, the resins were washed twice with ether and dried under vacuum. After this procedure was repeated, the resins were subjected to cleavage reaction by DDQ or deprotection of the Troc group.
32. All the yields were obtained after cleavage from the resin followed by purification by silica-gel column chromatography or preparative silica-gel TLC.
33. 2.
34. 4 as a catalyst.
35. Wakao, M.; Nakai, Y.; Fukase, K.; Kusumoto, S. Chem. Lett. 1999, 27.
36. 2. After Molecular Sieves 4Å beads were removed by picking with forceps, the resins were washed twice with ether and the resins were dried under vacuum. After this procedure was repeated two times, the resins were subjected to cleavage reaction by DDQ or deprotection of the Troc or TBDPS group.
37. 2.