An efficient route to optically active inositol derivatives via the resolution of myo-inositol 1,3,5-orthoformate: A short synthesis of D-myo-inositol-4-phosphate

Tetrahedron Asymmetry

Volumn 15, Issue 7, 2004, Pages 1193-1198

  Sureshan, Kana M ^a   Watanabe, Yutaka ^a  

^a EHIME UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; CHLORIDE; DEXTRO INOSITOL 4 PHOSPHATE; INOSITOL 1,3,5 ORTHOFORMATE; INOSITOL DERIVATIVE; O ACETYLMANDELOYL CHLORIDE; PHOSPHATE; UNCLASSIFIED DRUG;

ARTICLE; COLUMN CHROMATOGRAPHY; DIASTEREOISOMER; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR MECHANICS; OPTICS; PHASE SEPARATION; POLARIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; REACTION OPTIMIZATION; SYNTHESIS; TECHNIQUE;

EID: 1642587814     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.02.020     Document Type: Article

References (50)

1. Berridge M.J. Nature. 361:1993;315.
2. Hinchliffe K., Irvine R. Nature. 390:1997;123.
3. Bruzik K.S. Phosphoinositides: Chemistry, Biochemistry and Biomedical Applications. ACS Symposium Series 718. 1999.
4. Ferguson M.A.J., Williams A.F. Annu. Rev. Biochem. 57:1988;285.
5. Qiao L., Nan F., Kunkel M., Gallegos A., Kozikowski A.P. J. Med. Chem. 41:1998;3303.
6. Kozikowski A.P., Fauq A.H., Powis G., Aksoy I.A., Melder D.C., Aksoy S., Eichinger H. Cancer Chemother. Pharmacol. 29:1991;95.
7. Kozikowski A.P., Fauq A.H., Powis G., Aksoy I.A., Seewald M.J. J. Am. Chem. Soc. 112:1990;7403.
8. Hewitt M.C., Snyder D.A., Seeberger P.H. J. Am. Chem. Soc. 124:2002;13434.
9. Kwon Y.-K., Lee C., Chung S.-K. J. Org. Chem. 67:2002;3327.
10. Suzuki T., Suzuki S.T., Yamada I., Koashi Y., Yamada K., Chida N. J. Org. Chem. 67:2002;2874.
11. Chida N., Ogawa S. Chem. Commun. 1997;807. and references cited therein.
12. Suzuki T., Tanaka S., Yamada I., Koashi Y., Yamada K., Chida N. Org. Lett. 2:2000;1137.
13. Chida N., Yoshinaga M., Tobe T., Ogawa S. Chem. Commun. 1997;1043.
14. Akiyama T., Ohnari M., Shima H., Ozaki S. Synlett. 1991;831.
15. Sureshan K.M., Shashidhar M.S., Praveen T., Das T. Chem. Rev. 103:2003;4477.
16. Lee H.W., Kishi Y. J. Org. Chem. 50:1985;4402.
17. Baudin G., Glanzer B.L., Swaminathan K.S., Vasella A. Helv. Chim. Acta. 71:1988;1367.
18. Andersch P., Schneider M.P. Tetrahedron: Asymmetry. 4:1993;2135.
19. Praveen T., Shashidhar M.S. Carbohydr. Res. 330:2001;409.
20. Billington D.C., Baker R., Kulagowski J.J., Mawer I.M., Vacca J.P., deSolms S.J., Huff J.R. J. Chem. Soc., Perkin Trans. 1. 1989;1423.
21. Sureshan K.M., Shashidhar M.S. Tetrahedron Lett. 41:2000;4185. and references cited therein.
22. Sureshan K.M., Shashidhar M.S. Tetrahedron Lett. 42:2001;3037.
23. Sureshan K.M., Shashidhar M.S., Praveen T., Gonnade R.G., Bhadbhade M.M. Carbohydr. Res. 337:2002;2399.
24. Andersch P., Schneider M.P. Tetrahedron: Asymmetry. 7:1996;349.
25. Sarmah M.P., Shashidhar M.S. Carbohydr. Res. 338:2003;999.
26. Banerjee T., Shashidhar M.S. Tetrahedron Lett. 35:1994;8053.
27. Riley A.M., Mahon M.F., Potter B.V.L. Angew. Chem., Int. Ed. 36:1997;1472.
28. Riley A.M., Murphy C.T., Lindley C.J., Westwick J., Potter B.V.L. Bioorg. Med. Chem. Lett. 6:1996;2197.
29. Ballereau S., Poirier S.N., Guillemette G., Spiess B., Schlewer G. J. Chem. Soc., Perkin Trans. 1. 1998;1859.
30. Angyal S.J. Carbohydr. Res. 325:2000;313.
31. Sculibrene B.A., Miller S.J. J. Am. Chem. Soc. 123:2001;10125.
32. Sculibrene B.A., Morgan A.J., Miller S.J. J. Am. Chem. Soc. 124:2002;11653.
33. Sculibrene B.A., Morgan A.J., Miller S.J. Chem. Commun. 2003;1781.
34. Gilbert I.H., Holmes A.B., Young R.C. Tetrahedron Lett. 31:1990;2633.
35. Gilbert I.H., Holmes A.B., Pestchanker M.J., Young R.C. Carbohydr. Res. 234:1992;117.
36. Painter G.F., Grove S.J.A., Gilbert I.H., Holmes A.B., Raithby P.R., Hill M.L., Hawkins P.T., Stephens L.R. J. Chem. Soc., Perkin Trans. 1. 1999;923.
37. Schmitt L., Spiess B., Schlewer G. Tetrahedron Lett. 39:1998;4817.
38. Yeh S.-M., Lee G.H., Wang Y., Luh T.-Y. J. Org. Chem. 62:1997;8315.
39. Ozaki S., Lie L. Witczak Z.J., Neiforth K.A. Carbohydrates in Drug Design. 1997;343 Mercel Dekker, New York.
40. Bruzik K.S., Myers J., Tsai M.-D. Tetrahedron Lett. 33:1992;1009.
41. Yu K.-L., Fraser-Reid B. Tetrahedron Lett. 29:1988;979.
42. Vacca J.P., deSolms S.J., Huff J.R., Billington D.C., Baker R., Kulagowski J.J., Mawer I.M. Tetrahedron. 45:1989;5679.
43. Corrigendum Vacca J.P., deSolms S.J., Huff J.R., Billington D.C., Baker R., Kulagowski J.J., Mawer I.M. Tetrahedron. 47:1991;907.
44. Sureshan K.M., Shashidhar M.S., Varma A.J. J. Org. Chem. 67:2002;6884. and references cited therein.
45. Hosoda A., Miyake Y., Nomura E., Taniguchi H. Chem. Lett. 32:2003;1042.
46. Akiyama T., Hara M., Fuchibe K., Sakamoto S., Yamaguchi K. Chem. Commun. 2003;1734.
47. Sureshan K.M., Gonnade R.G., Shashidhar M.S., Puranik V.G., Bhadbhade M.M. Chem. Commun. 2001;881.
48. Akiyama T., Nishimoto H., Ishikawa K., Ozaki S. Chem. Lett. 1992;447.
49. Akiyama T., Horiguchi N., Ida T., Ozaki S. Chem. Lett. 1995;975.
50. Ozaki S., Kondo Y., Shiotani N., Ogasawara T., Watanabe Y. J. Chem. Soc., Perkin Trans. 1. 1992;729.