Thermal epimerization of inositol 1,3-benzylidene acetals in the molten state

Tetrahedron

Volumn 67, Issue 38, 2011, Pages 7280-7288

  Gurale, Bharat P ^a   Krishnaswamy, Shobhana ^a   Vanka, Kumar ^a   Shashidhar, Mysore S ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Cyclitols; Deoxygenation; Epimerization; Melt; Xanthate

Indexed keywords

1,3 O BENZYLIDENE 2,4,5,6 TETRA O SUBSTITUTED MYO INOSITOL DERIVATIVE; ACETAL DERIVATIVE; INOSITOL 1,3 BENZYLIDENE ACETAL DERIVATIVE; INOSITOL DERIVATIVE; MYO INOSITOL 1,3,5 ORTHOBENZOATE DERIVATIVE; UNCLASSIFIED DRUG; XANTHIC ACID DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CRYSTALLIZATION; DEOXYGENATION; EPIMERIZATION; HEATING; ISOMERIZATION; MELTING POINT; PRIORITY JOURNAL; RADICAL REACTION; X RAY CRYSTALLOGRAPHY;

TETRA;

EID: 80051791383     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.07.044     Document Type: Article

References (77)

1. I.C. Paul, and D.Y. Curtin Acc. Chem. Res. 6 1973 217 225
2. B.S. Green, M. Lahav, and D. Rabinovich Acc. Chem. Res. 12 1979 191 197
3. V.E. Shklover, and T.V. Timofeeva Russ. Chem. Rev. 54 1985 619 644
4. V. Ramamurthy, and K. Venkatesan Chem. Rev. 87 1987 433 481
5. Y. Ito Synthesis 1 1998 1 32
6. A.E. Keating, and M.A. Garcia-Garibay V. Ramamurthy, K. Schanze, Molecular and Supramolecular Photochemistry Vol. 2 1998 Marcel Dekker New York, NY 195 248
7. D. Braga, and F. Grepioni Angew. Chem., Int. Ed. 43 2004 4002 4011
8. D. Braga, and F. Grepioni Chem. Commun. 2005 3635 3645
9. H. Koshima, H. Kawanishi, M. Nagano, H. Yu, M. Shiro, T. Hosoya, H. Uekusa, and Y. Ohashi J. Org. Chem. 70 2005 4490 4497
10. C.J. Mortko, and M.A. Garcia-Garibay S.E. Denmark, J.S. Siegel, Topics in Stereochemistry Vol. 25 2006 John Hoboken, NJ, USA 205 253
11. G. Kaupp S.E. Denmark, J.S. Siegel, Topics in Stereochemistry Vol. 25 2006 John Hoboken, NJ, USA 303 350
12. T. Odani, S. Okada, C. Kabuto, T. Kimura, S. Shimada, H. Matsuda, H. Oikawa, A. Matsumoto, and V. Nakanishi Cryst. Growth Des. 9 2009 3481 3487
13. J. Harada, M. Harakawa, S. Sugiyama, and K. Ogawa CrystEngComm 11 2009 1235 1239
14. R. Destro, E. Ortoleva, R. Soave, L. Loconte, and L.L. Presti Phys. Chem. Chem. Phys. 11 2009 7181 7188
15. D. Cantillo, M. Avalos, R. Babiano, P. Cintas, J.L. Jimenez, M.E. Light, and J.C. Palacios J. Org. Chem. 75 2010 4300 4303
16. M.W. Ghosn, and C. Wolf J. Org. Chem. 75 2010 6653 6659
17. R.G. Gonnade, S. Iwama, Y. Mori, H. Takahashi, H. Tsue, and R. Tamura Cryst. Growth Des. 11 2011 607 615 and references cited therein
18. B. Mondal, B. Captain, and V. Ramamurthy Photochem. Photobiol. Sci. 10 2011 891 894
19. M. Epple, S. Ebbinghaus, A. Reller, U. Gloistein, and H.K. Cammenga Thermochim. Acta 269/270 1995 433 441
20. G. Rothenberg, A.P. Downie, C.L. Raston, and J.L. Scott J. Am. Chem. Soc. 123 2001 8701 8708
21. G. Kaupp Top. Curr. Chem. 254 2005 95 183
22. F. Toda Acc. Chem. Res. 28 1995 480 486
23. J.O. Metzger Angew. Chem., Int. Ed. 37 1998 2975 2978
24. A. Loupy Top. Curr. Chem. 206 1999 153 207
25. K. Tanaka, and F. Toda Chem. Rev. 100 2000 1025 1074
26. G.W.V. Cave, C.L. Raston, and J.L. Scott Chem. Commun. 2001 2159 2169
27. M. Kaftory F. Toda, Organic Solid State Reaction 2002 Kluwer Academic Dordrecht 47 67
28. S. Nakamatsu, K. Yoshizawa, S. Toyota, F. Toda, and I. Matijasic Org. Biomol. Chem. 1 2003 2231 2234
29. G. Kaupp, M.R. Naimi-Jamal, and J. Schmeyers Tetrahedron 59 2003 3753 3760
30. S. Matsumoto, K. Kumazawa, and K. Ogura Bull. Chem. Soc. Jpn. 76 2003 2179 2182
31. X. Bu, H. Jing, L. Wang, T. Chang, L. Jin, and Y. Liang J. Mol. Catal. A: Chem. 259 2006 121 124
32. B. Rodriguez, A. Bruckmann, T. Rantanen, and C. Bolm Adv. Synth. Catal. 349 2007 2213 2233
33. I. Pravst, M. Zupan, and S. Stavber Tetrahedron 64 2008 5191 5199
34. O. Dolotko, J.Z. Wiench, K.W. Dennis, V.K. Pecharsky, and V.P. Balema New J. Chem. 34 2010 25 28
35. A. Broido, Y. Houminer, and S. Patai J. Chem. Soc. B 1966 411 414
36. R.E. Pincock, K.R. Wilson, and T.E. Kiovsky J. Am. Chem. Soc. 89 1967 6890 6897
37. M. Krasnoselsky, and S. Patai J. Chem. Soc. B 1969 24 27
38. M. Michman, and M. Frenkel J. Chem. Soc. C 1971 3856 3859
39. G. Kaupp, and M.R. Naimi-Jamal Eur. J. Org. Chem. 2002 1368 1373
40. M.F. Beristain, S. Fomine, and T. Ogawa Mol. Cryst. Liq. Cryst. 447 2006 251 263
41. G. Kaupp J. Phys. Org. Chem. 21 2008 630 643
42. C. Murali, M.S. Shashidhar, R.G. Gonnade, and M.M. Bhadbhade Chem. - Eur. J. 15 2009 261 269 and references cited there in
43. R. Sakurai, S. Suzuki, J. Hashimoto, M. Baba, O. Itoh, A. Uchida, T. Hattori, S. Miyano, and M. Yamaura Org. Lett. 6 2004 2241 2244
44. R. Sakurai, O. Itoh, A. Uchida, T. Hattori, S. Miyano, and M. Yamaura Tetrahedron 60 2004 10553 10557 For an example of epimerization in solution
45. N. Ikuma, H. Tsue, N. Tsue, S. Shimono, Y. Uchida, K. Masaki, N. Matsuoka, and R. Tamura Org. Lett. 7 2005 1797 1800
46. R.H. Michell Biochim. Biophys. Acta 415 1975 81 87
47. M.J. Berridge, and R.F. Irvine Nature 312 1984 315 321
48. B.V.L. Potter Nat. Prod. Rep. 7 1990 1 24
49. R. Katso, K. Okkenhaug, K. Ahmadi, S. White, J. Timms, and M.D. Waterfield Annu. Rev. Cell Dev. Biol. 17 2001 615 675
50. K.M. Nicholson, and N.G. Anderson Cell. Signalling 14 2002 381 395
51. A.M. Shamsuddin, and I. Vucenic Curr. Cancer Ther. Rev. 1 2005 259 269
52. M.P. Wymann, and R. Schneiter Nat. Rev. 9 2008 162 176
53. X. Liu, E.C. Moody, S.S. Hecht, and S.J. Sturla Bioorg. Med. Chem. 16 2008 3419 3427
54. K.M. Sureshan, A.M. Riley, A.M. Rossi, S.C. Tovey, S.G. Dedos, C.W. Taylor, and B.V.L. Potter Chem. Commun. 2009 1204 1206 and references cited there in
55. I.H. Gilbert, A.B. Holmes, M.J. Pestchanker, and R.C. Young Carbohydr. Res. 234 1992 117 130
56. C. Murali, M.S. Shashidhar, and C.S. Gopinath Tetrahedron 63 2007 4149 4155
57. J.M. Swarbrick, S. Cooper, G. Bultynck, and P.R.J. Gaffney Org. Biomol. Chem. 7 2009 1709 1715
58. R.C. Jagdhane, and M.S. Shashidhar Eur. J. Org. Chem. 2010 2945 2953
59. J.M. Swarbrick, and P.R.J. Gaffney J. Org. Chem. 75 2010 4376 4386
60. G. Bhosekar, C. Murali, R.G. Gonnade, M.S. Shashidhar, and M.M. Bhadbhade Cryst. Growth Des. 5 2005 1977 1982
61. C. Murali, B.P. Gurale, and M.S. Shashidhar Eur. J. Org. Chem. 2010 755 764
62. Further increase in the reaction temperature led to increased formation of the diol 14, 2-O-(4-methoxybenzyl)-4,6-di-O-benzyl-5-O-(methylthio) thiocarbonyl myo-inositol. As observed during the epimerization of 8, formation of minor amounts of the diols 13 [2,4,6-tri-O-benzyl-5-O-[(methylthio) thiocarbonyl] myo-inositol] and 15 [1,3,5-tri-O-benzyl-2-O-[(methylthio) thiocarbonyl] neo-inositol] were observed during the epimerization of 7 and 9.
63. R. Ahlrichs, M. Bär, H.-P. Baron, R. Bauernschmitt, S. Böcker, M. Ehrig, K. Eichkorn, S. Elliott, F. Furche, F. Haase, M. Häser, H. Horn, C. Huber, U. Huniar, M. Kattannek, C. Kölmel, M. Kollwitz, K. May, C. Ochsenfeld, H. Öhm, A. Schäfer, U. Schneider, O. Treutler, M. von Arnim, F. Weigend, P. Weis, and H. Weiss TURBOMOLE (Version 5.3) 2000 Universität Karlsruhe Karlsruhe, Germany
64. A. Schäfer, C. Huber, and R. Ahlrichs J. Chem. Phys. 100 1994 5829 5835
65. D. Andrae, U. Haeussermann, M. Dolg, H. Stoll, and H. Preuss Theor. Chim. Acta 77 1990 123 141
66. Hyperchem (version 5); Hypercube, Gainesville, FL, 32601.
67. A.D. Becke Phys. Rev. A: At., Mol., Opt. Phys. 38 1988 3098 3100
68. J.P. Perdew Phys. Rev. B: Condens. Matter Mater. Phys. 33 1986 8822 8824
69. A. Schäfer, H. Horn, and R. Ahlrichs J. Chem. Phys. 97 1992 2571 2577
70. K. Eichkorn, O. Treutler, H. Öhm, M. Häser, and R. Ahlrichs Chem. Phys. Lett. 240 1995 283 290
71. M. Sierka, A. Hogekamp, and R. Ahlrichs J. Chem. Phys. 118 2003 9136 9148
72. D.D. Perrin, and W.L.F. Armarego Purification of Laboratory Chemicals 2nd ed. 1988 Pergamon Oxford, UK
73. Bruker SADABS (Version 2.05), SMART (Version 5.631) and SAINT (Version 6.45) 2003 Bruker AXS Madison, Wisconsin, USA
74. G.M. Sheldrick Acta Crystallogr., Sect. A: Found. Crystallogr. 64 2008 112 122
75. L.J. Farrugia J. Appl. Crystallogr. 30 1997 565
76. C.F. Macrae, P.R. Edgington, P. McCabe, E. Pidcock, G.P. Shields, R. Taylor, M. Towler, and J. van de Streek J. Appl. Crystallogr. 39 2006 453 457
77. A.L. Spek J. Appl. Crystallogr. 36 2003 7 13