Synthesis of ether-linked sugar by nucleophilic opening of carbohydrate oxiranes

Synthesis

Volumn , Issue 23, 2008, Pages 3761-3768

  Nishiyama, Kazusa ^a   Nakayama, Takahiro ^a   Natsugari, Hideaki ^a   Takahashi, Hideyo ^a  

^a TEIKYO UNIVERSITY   (Japan)

Author keywords

Carbohydrates; Epoxides; Ethers; Regio selectivity; Ring opening

Indexed keywords

BIOMOLECULES; CARBOHYDRATES; ETHERS; REGIOSELECTIVITY; SUGAR (SUCROSE); SUGARS; SULFUR COMPOUNDS;

EPOXIDES; MANNOPYRANOSIDES; NUCLEOPHILIC RINGS; OPENING REACTIONS; OXIRANE; OXIRANES; RING OPENING; SYNTHESIS OF;

ORGANIC COMPOUNDS;

ALLOPYRANOSIDE; ALPHA OXIRANE; BETA OXIRANE; CARBOHYDRATE; ETHER; ETHYLENE OXIDE; ETHYLENE OXIDE DERIVATIVE; NUCLEOPHILE; SUGAR; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; REGIOSELECTIVITY; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

EID: 57549095167     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1083221     Document Type: Article

References (45)

1. Pérez, S.; Pérez, R. M.; Pérez, C.; Zavala, M. A.; Vargas, R. Pharm. Acta Helv. 1997, 72, 105.
2. (a) Haines, A. H. Tetrahedron Lett. 2004, 45, 835.
3. (b) Haines, A. N. Org. Biomol. Chem. 2004, 2, 2352.
4. (c) Cumpstey, I. Synlett 2006, 1711.
5. (d) Ogawa, S.; Matsunaga, N.; Li, H.; Palcic, M. M. Eur. J. Org. Chem. 1999, 631.
6. (e) Hodosi, G.; Kovac, P. Carbohydr. Res. 1998, 308, 63.
7. (f) Whistler, R. L.; Frowein, A. J. Org. Chem. 1961, 26, 3946.
8. Takahashi, H.; Fukuda, T.; Mitsuzuka, H.; Namme, R.; Miyamoto, H.; Ohkura, Y.; Ikegami, S. Angew. Chem. Int. Ed. 2003, 42, 5069.
9. Takahashi, H.; Mitsuzuka, H.; Nishiyama, K.; Ikegami, S. Synthesis 2006, 1415.
10. (a) Williams, N. R. Adv. Carbohydr. Chem. 1970, 25, 109.
11. (b) Rehnberg, N.; Magnusson, G. J. Org. Chem. 1990, 55, 5467.
12. (c) Boullanger, P.; Descotes, G. Glycoscience 2001, 1, 253.
13. (a) Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661.
14. (b) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380.
15. For 1,6-anhydro sugars, see: (a) Hung, S.-C.; Wang, C.-C.; Chang, S.-W.; Chen, C.-S. Tetrahedron Lett. 2001, 42, 1321.
16. (b) Hung, S.-C.; Thopate, S. R.; Chi, F.-C.; Cheng, S.-W.; Lee, J.-C.; Wang, C.-C.; Wen, Y.-S. J. Am. Chem. Soc. 2001, 123, 3153.
17. For 2,3-anhydro sugars, see: (c) Nogami, Y.; Nasu, K.; Koga, T.; Ohta, K.; Fujita, K.; Immel, S.; Lindner, H. J.; Schmitt, G. E.; Lichtenthaler, F. W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1899.
18. (d) Chiu, S.-H.; Myles, D. C.; Garrell, R. L.; Stoddart, J. F. J. Org. Chem. 2000, 65, 2792.
19. (e) Callam, C. S.; Gadikota, R. R.; Lowary, T. L. Synlett 2003, 1271.
20. (f) Callam, C. S.; Gadikota, R. R.; Krein, D. M.; Lowary, T. L. J. Am. Chem. Soc. 2003, 125, 13112.
21. (a) Hirota, K.; Takasu, H.; Sajiki, H. Heterocycles 2000, 52, 1329.
22. (b) Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745.
23. (c) Roussev, C. D.; Simeonov, M. F.; Petkov, D. D. J. Org. Chem. 1997, 62, 5238.
24. (a) Fürst, A.; Plattner, P. A. Abstracts of Papers of the 12th International Congress of Pure and Applied Chemistry; New York, 1951, 409.
25. (b) Angyal, S. J. Chem. Ind. 1954, 222, 1230.
26. (c) Cookson, R. C. Chem. Ind. 1953, 223, 1512.
27. (d) Eliel, E. L.; Allinger, N. L.; Angyal, S. J.; Morrison, G. A. Conformational Analysis; Wiley: New York, 1965.
28. A detailed analysis of the regiospecificity of the nucleophilic ring opening of oxiranes was reported: (a) Crotti, P.; Bussolo, V. D.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron 2002, 58, 6069.
29. (b) Crotti, P.; Renzi, G.; Favero, L.; Roselli, G.; Bussolo, V. D.; Caselli, M. Tetrahedron 2003, 59, 1453.
30. (a) Abdel-Malik, M. M.; Perlin, A. S. Carbohydr. Res. 1989, 190, 39.
31. (b) Knapp, S.; Naughton, A. B. J.; Jaramillo, C.; Pipik, B. J. Org. Chem. 1992, 57, 7328.
32. Wu, X.; Kong, F.; Lu, D.; Li, G. Carbohydr. Res. 1992, 235, 163.
33. Lipták, A.; Jodal, I.; Nanasi, P. Carhohydr. Res. 1975, 44, 1.
34. In every reaction, the theoretical amount of alcohol was recovered almost completely.
35. The product was derivatized as its acetate to confirm the structure.
36. Du, Y.; Mao, W.; Kong, F. Carbohydr. Res. 1996, 282, 315.
37. Koto, S.; Takebe, Y.; Zen, S. Bull. Chem. Soc. Jpn. 1972, 45, 291.
38. Inch, T. D.; Lewis, G. J. Carbohydr. Res. 1972, 22, 91.
39. For the effect of TMU, see: (a) Imagawa, H.; Fujikawa, Y.; Tsuchihiro, A.; Kinoshita, A.; Yoshinaga, T.; Takao, H.; Nishizawa, M. Synlett 2006, 639.
40. (b) Imagawa, H.; Iyenaga, T.; Nishizawa, M. Org. Lett. 2005, 7, 451.
41. (c) Nishizawa, M.; Takao, H.; Yadav, V. K.; Imagawa, H.; Sugihara, T. Org. Lett. 2003, 5, 4563.
42. TMSOTf might be deactivated by partially deprotected oxirane and product, which would lower the yield of 12.
43. Shie, C.-R.; Tzeng, Z.-H.; Kulkarni, S.-S.; Uang, B.-J.; Hsu, C.-Y.; Hung, S.-C. Angew. Chem. Int. Ed. 2005, 44, 1665.
44. Weng, S.-S.; Lin, Y.-D.; Chen, C.-T. Org. Lett. 2006, 8, 5633.
45. Yamanoi, T.; Iwai, Y.; Inazu, T. Heterocycles 2000, 53, 1263.