Vinyl sulfone-modified carbohydrates: an inconspicuous group of chiral building blocks

Tetrahedron

Volumn 64, Issue 17, 2008, Pages 3605-3628

  Pathak, Tanmaya ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

Acetylenic sulfone; Aminosugars; Branched chain sugar; Carbohydrates; Divinyl sulfone; Michael addition; Nucleosides; Vinyl sulfone

Indexed keywords

1 SULFONYLGLYCAL DERIVATIVE; 2 PHENYLSULFONYL 1 2 TRIMETHYLSILYL VINYL; 2 SULFONYLGLYCAL DERIVATIVE; 2 SULFONYLHEX 2 ENOPYRANOSIDE DERIVATIVE; AMINOSUGAR; CARBOHYDRATE; FURAN DERIVATIVE; HEX 2 ENOFURANOSIDE DERIVATIVE; LIVIDOSAMINE DERIVATIVE; PENT 2 ENOFURANOSIDE DERIVATIVE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYLSULFONE DERIVATIVE;

CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; MICHAEL ADDITION; PRIORITY JOURNAL; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

EID: 40849141834     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.01.069     Document Type: Review

References (95)

1. Fuchs P.L., and Braish T.F. Chem. Rev. 86 (1986) 903-918
2. In: Patai S., Rappoport Z., and Stirling C. (Eds). The Chemistry of Sulphones and Sulphoxides (1988), John Wiley and Sons, New York, NY
3. Simpkins N.S. Tetrahedron 46 (1990) 6951-6984
4. Simpkins N.S. Sulphones in Organic Synthesis (1993), Pergamon, Oxford
5. Forristal I. J. Sulf. Chem. 26 (2005) 163-195
6. Isobe M. Stud. Org. Chem. 28 (1987) 209-229
7. Padwa A., and Murphree S.S. Rev. Het. Chem. 6 (1992) 241-262
8. Padwa A., Ni Z., and Watterson S.H. Pure Appl. Chem. 68 (1996) 831-836
9. Carretero J.C., Arrayas R.G., Buezo N.D., Garrido J.L., Alonso I., and Adrio J. Phosphorus, Sulfur Silicon Relat. Elem. 153-154 (1999) 259-273
10. Aggarwal V.K., Ali A., and Coogan M.P. Tetrahedron 55 (1999) 293-312
11. Arjona O., and Plumet J. Rec. Res. Dev. Org. Chem. 3 (1999) 265-295
12. Silveira C.C., Perin G., Jacob R.G., and Braga A.L. Phosphorus, Sulfur Silicon Relat. Elem. 171-172 (2001) 309-354
13. Stadnichuk M.D. Russ. J. Gen. Chem. 73 (2003) 1751-1768
14. Schaffner A.-P., and Renaud P. Eur. J. Org. Chem. (2004) 2291-2298
15. Srikanth G.S.C., and Castle S.L. Tetrahedron 61 (2005) 10377-10441
16. Meadows D.C., and Gervay-Hague J. Med. Res. Rev. 26 (2006) 793-814
17. Najera C., and Yus M. Tetrahedron 55 (1999) 10547-10658
18. Hanessian S. Total Synthesis of Natural Products: The 'Chiron' Approach (1983), Marcel Dekker, New York, NY
19. Crosby J. Tetrahedron 47 (1991) 4789-4846
20. Cintas P. Tetrahedron 47 (1991) 6079-6111
21. Sheldon R.A. Chirotechnology Industrial Synthesis of Optically Active Compounds (1993), Marcel Dekker, New York, NY
22. Collins P.M., and Ferrier R.J. Monosaccharides: Their Chemistry and Their Roles in Natural Products (1996), John Wiley and Sons, Chichester, UK
23. Hollingsworth R.I., and Wang G. Chem. Rev. 100 (2000) 4267-4282
24. Ramesh N.G., and Balasubramanian K.K. Eur. J. Org. Chem. (2003) 4477-4487
25. Sharma G.V.M., and Krishna P.R. Curr. Org. Chem. 8 (2004) 1187-1209
26. Marot C., and Rollin P. Phosphorus, Sulfur Silicon Relat. Elem. 95-96 (1994) 503-504
27. Pathak T. Vinylsulfone-modified Carbohydrates: Synthesis and Properties in Trends in Carbohydrate Chemistry Vol. 6 (2000) pp 65-78 (CAN 141:366372)
28. Sanki A., and Pathak T. Proc. Indian Nat. Sci. Acad. 71A (2005) 245-266
29. Tronchet J.M.J., and Baehler B. Helv. Chim. Acta 54 (1971) 546-553
30. Tronchet J.M.J., and Baehler Br. Helv. Chim. Acta 55 (1972) 2112-2120
31. Tronchet J.M.J., Baehler B., Eder H., Le-Hong N., Perret F., Poncet J., and Zumwald J.B. Helv. Chim. Acta 56 (1973) 1310-1317
32. Isobe M., Kitamura M., and Goto T. J. Am. Chem. Soc. 104 (1982) 4997-4999
33. Kitamura M., Isobe M., Ichikawa Y., and Goto T. J. Am. Chem. Soc. 106 (1984) 3252-3257
34. Wu J.C., Pathak T., Tong W., Vial J.M., Remaud G., and Chattopadhyaya J. Tetrahedron 44 (1988) 6705-6722
35. Bera S., Sakthivel K., Langley G.J., and Pathak T. Tetrahedron 51 (1995) 7857-7866
36. Bera S., Langley G.J., and Pathak T. J. Org. Chem. 63 (1998) 1754-1760
37. Ravindran B., Sakthivel K., Suresh C.G., and Pathak T. J. Org. Chem. 65 (2000) 2637-2641
38. Suresh C.G., Ravindran B., Rao K.N., and Pathak T. Acta Crystallogr. C56 (2000) 1030-1032
39. Ravindran B., Deshpande S.G., and Pathak T. Tetrahedron 57 (2001) 1093-1098
40. Ravindran B., and Pathak T. Indian J. Chem. 41B (2002) 1114-1120
41. [Errata:. Indian J. Chem. 41B (2002) 1100 ]
42. Suresh C.G., Ravindran B., Pathak T., Rao K.N., Shashidharaprasad J., and Lokanath N.K. Carbohydr. Res. 337 (2002) 1507-1512
43. Sanki A.K., and Pathak T. Synlett (2002) 1241-1244
44. [Errata:. Synlett (2002) 1560 ]
45. Sanki A.K., and Pathak T. Tetrahedron 59 (2003) 7203-7214
46. Sanki A.K., Suresh C.G., Falgune U.D., and Pathak T. Org. Lett. 5 (2003) 1285-1288
47. Bera S., and Pathak T. Synlett (2004) 2147-2150
48. Pathak T. Eur. J. Org. Chem. (2004) 3361
49. Das I., Pathak T., and Suresh C.G. J. Org. Chem. 70 (2005) 8047-8054
50. Das I., and Pathak T. Org. Lett. 8 (2006) 1303-1306
51. Das, I. Synthesis and Synthetic Applications of Endocyclic and Exocyclic Vinyl Sulfone-Modified Furanosides. Ph.D. Thesis; Indian Institute of Technology: Kharagpur, India, 2007.
52. Das I., Pathak T., and Suresh C.G. J. Org. Chem. 72 (2007) 5523-5533
53. Ferrier R.J., Furneaux R.H., and Tyler P.C. Carbohydr. Res. 58 (1977) 397-404
54. Cassidy J.F., and Williams J.M. Tetrahedron Lett. 27 (1986) 4355-4358
55. Lesimple P., Beau J.-M., Jaurand G., and Sinay P. Tetrahedron Lett. 27 (1986) 6201-6204
56. Dubois E., and Beau J.-M. Carbohydr. Res. 228 (1992) 103-120
57. Gunn A., Jarowicki K., Kocienski P., and Lockhart S. Synthesis (2001) 331-338
58. Qiu D., and Schmidt R.R. Synthesis (1990) 875-877
59. Qiu D., and Schmidt R.R. Carbohydr. Lett. 1 (1995) 291-298
60. Sakakibara T., Yamamoto A., and Ishido Y. Carbohydr. Res. 179 (1988) 77-86
61. Frische K., and Schmidt R.R. Liebigs Ann. Chem. (1994) 297-303
62. Schmidt R.R., and Preuss R. Tetrahedron Lett. 30 (1989) 3409-3412
63. Takai I., Yamamoto A., Ishido Y., Sakakibara T., and Yagi E. Carbohydr. Res. 220 (1991) 195-207
64. Sakakibara T., Takaib I., Yamamoto A., Iizuka H., Hirasawa K., and Ishido Y. Tetrahedron Lett. 31 (1990) 3749-3752
65. Holzapfel C.W., Portwig M., and Williams D.B.G.S. Afr. J. Chem. 52 (1999) 165-167
66. Sakakibara T., Takai I., Tachimori Y., Yamamoto A., Ishido Y., and Sudoh R. Carbohydr. Res. 160 (1987) c3-c5
67. Sakakibara T., Takai I., Yamamoto A., Tachimori Y., Sudoh R., and Ishido Y. Carbohydr. Res. 169 (1987) 189-199
68. Sakakibara T., Shindo T., and Hirai H. Carbohydr. Res. 337 (2002) 2061-2067
69. Trost B.M., Seoane P., Mignani S., and Acemoglu M. J. Am. Chem. Soc. 111 (1989) 7487-7500
70. Holzapfel C.W., and van der Merwe T.L. Tetrahedron Lett. 37 (1996) 2303-2306
71. Welch C.J., Bazin H., and Chattopadhyaya J. Acta Chem. Scand. B40 (1986) 343-357
72. Williams N.R. Adv. Carbohydr. Chem. Biochem. 25 (1970) 109-173
73. Sakakibara T., Suzuki K., Sakai A., Shindo M., Nagano C., Narumi S., Kajihara Y., and Mochizuki K. Tetrahedron Lett. 44 (2003) 5711-5714
74. Zhang H.C., Brakta M., and Daves Jr. G.D. Tetrahedron Lett. 34 (1993) 1571-1574
75. Wee A.G.H., McLeod D.D., and Rankin T.J. Heterocycles 48 (1998) 2263-2278
76. Wee A.G.H., and McLeod D.D. J. Org. Chem. 68 (2003) 6268-6273
77. Kawana M., and Kuzuhara H. Synthesis (1995) 544-552
78. Trost B.M., and Grese T.A. J. Org. Chem. 56 (1991) 3189-3192
79. Kawauchi N. Carbohydr. Lett. 3 (1998) 199-202
80. Barton D.H.R., Gero S.D., Quiclet-Sire B., and Samadi M. J. Chem. Soc., Chem. Commun. (1988) 1372-1373
81. Musicki B., and Widlanski T.S. Tetrahedron Lett. 32 (1991) 1267-1270
82. Barnes N.J., Davidson A.H., Hughes L.R., and Procter G. J. Chem. Soc., Chem. Commun. (1985) 1292-1294
83. Marot C., and Rollin P. Tetrahedron Lett. 35 (1994) 8377-8380
84. Diez D., Beneitez M.T., Marcos I.S., Garrido N.M., Basabe P., and Urones J.G. Tetrahedron: Asymmetry 13 (2002) 639-646
85. Diez D., Beneitez M.T., Marcos I.S., Garrido N.M., Basabe P., Sanz F., Broughton H.B., and Urones J.G. Org. Lett. 5 (2003) 4361-4364
86. Alonso-Cruz C.R., Leon E.I., Ortiz-Lopez F.J., Rodriguez M.S., and Suarez E. Tetrahedron Lett. 46 (2005) 5265-5268
87. (Errata:. Tetrahedron Lett. 47 (2006) 1359 )
88. Pathak T. Chem. Rev. 102 (2002) 1623-1667
89. Onuma S., Kumamoto H., Kawato M., and Tanaka H. Tetrahedron 58 (2002) 2497-2503
90. Wnuk S.F., Yuan C.-S., Borchardt R.T., Balzarini J., De Clercq E., and Robins M.J. J. Med. Chem. 37 (1994) 3579-3587
91. Acena J.L., Arjona O., Fernandez de la Pradilla R., Plumet J., and Viso A. J. Org. Chem. 57 (1992) 1945-1946
92. Acena J.L., Arjona O., Fernandez de la Pradilla R., Plumet J., and Viso A. J. Org. Chem. 59 (1994) 6419-6424
93. Acena J.L., Arjona O., and Plumet J. J. Org. Chem. 62 (1997) 3360-3364
94. Arjona O., Lorenzo G., Medel R., and Plumet J. Tetrahedron Lett. 42 (2001) 7041-7043
95. Marquis R.W. Annu. Rep. Med. Chem. 39 (2004) 79-98