-
3
-
-
85031175933
-
-
For some recent references, see: (a) Swamy, N. R.; Venkateswarlu, Y. Synthesis 2002, 598-600; (b) Takhi, M.; Abdel-Rahman, A. A.-H.; Schmidt, R. R. Synlett 2001, 427-429; (c) Masson, C.; Soto, J.; Bessodes, M. Synlett 2000, 1281-1282
-
For some recent references, see: (a) Swamy, N. R.; Venkateswarlu, Y. Synthesis 2002, 598-600; (b) Takhi, M.; Abdel-Rahman, A. A.-H.; Schmidt, R. R. Synlett 2001, 427-429; (c) Masson, C.; Soto, J.; Bessodes, M. Synlett 2000, 1281-1282.
-
-
-
-
4
-
-
85031176173
-
-
For examples, see: (a) Levy, D. E.; Tang, C. The Chemistry of C-Glycosides; Pergamon Press: Oxford, 1995; (b) Danishefsky, S. J.; DeNinno, S.; Lartey, P. J. Am. Chem. Soc. 1987, 109, 2082-2089; (c) Ichikawa, Y.; Isobe, M.; Konobe, M.; Goto, T. Carbohydr. Res. 1987, 171, 193-199; (d) Hannessian, S. Total Synthesis of Natural Products: The 'Chiron' Approach; Pergamon Press: Oxford, 1993
-
For examples, see: (a) Levy, D. E.; Tang, C. The Chemistry of C-Glycosides; Pergamon Press: Oxford, 1995; (b) Danishefsky, S. J.; DeNinno, S.; Lartey, P. J. Am. Chem. Soc. 1987, 109, 2082-2089; (c) Ichikawa, Y.; Isobe, M.; Konobe, M.; Goto, T. Carbohydr. Res. 1987, 171, 193-199; (d) Hannessian, S. Total Synthesis of Natural Products: The 'Chiron' Approach; Pergamon Press: Oxford, 1993.
-
-
-
-
11
-
-
0035829356
-
-
For a synthetic route to furanoid glycals via selenoxide elimination, see:
-
For a synthetic route to furanoid glycals via selenoxide elimination, see: Bravo F., Kassou M., Díaz Y., Castillón S. Carbohydr. Res. 336:2001;83-97.
-
(2001)
Carbohydr. Res.
, vol.336
, pp. 83-97
-
-
Bravo, F.1
Kassou, M.2
Díaz, Y.3
Castillón, S.4
-
12
-
-
0037193164
-
-
For a recent paper on the use of thioglycosides for the synthesis of 2-hydroxy and 2-amino glycals that was published during the course of this work, see:
-
For a recent paper on the use of thioglycosides for the synthesis of 2-hydroxy and 2-amino glycals that was published during the course of this work, see: Liu J., Huang C.-H., Wong C.-H. Tetrahedron Lett. 43:2002;3447-3448.
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 3447-3448
-
-
Liu, J.1
Huang, C.-H.2
Wong, C.-H.3
-
14
-
-
0001539371
-
-
Reich H.J., Wollowitz S., Trend J.E., Chow F., Wendelborn D.F. J. Org. Chem. 43:1978;1697-1705.
-
(1978)
J. Org. Chem.
, vol.43
, pp. 1697-1705
-
-
Reich, H.J.1
Wollowitz, S.2
Trend, J.E.3
Chow, F.4
Wendelborn, D.F.5
-
18
-
-
85031162005
-
-
Required to prevent side reactions caused by selenenic acids and their disproportionation products.
-
Required to prevent side reactions caused by selenenic acids and their disproportionation products.
-
-
-
-
20
-
-
85031168546
-
-
19 all possess spectroscopic data consistent with those found in the literature
-
19 all possess spectroscopic data consistent with those found in the literature.
-
-
-
-
21
-
-
85031169587
-
-
3a-f, 1 equiv.) and N,N-diisopropylethylamine (1.7 equiv.) were dissolved in anhydrous dichloromethane and the solution cooled to 0°C. tert-Butyl hydroperoxide (5.5 M solution in decane, 2.3 equiv.) was added drop-wise over a period of 5 min, and then titanium(IV) isopropoxide (1.0 equiv.) was added. The reaction mixture was stirred under an atmosphere of argon for 2 h, after which time TLC (petrol:ethyl acetate, 4:1) indicated complete consumption of starting material. The yellow solution was concentrated in vacuo, and purified by flash column chromatography
-
Typical experimental procedure: The selenoglycoside ( 3a-f, 1 equiv.) and N,N-diisopropylethylamine (1.7 equiv.) were dissolved in anhydrous dichloromethane and the solution cooled to 0°C. tert-Butyl hydroperoxide (5.5 M solution in decane, 2.3 equiv.) was added drop-wise over a period of 5 min, and then titanium(IV) isopropoxide (1.0 equiv.) was added. The reaction mixture was stirred under an atmosphere of argon for 2 h, after which time TLC (petrol:ethyl acetate, 4:1) indicated complete consumption of starting material. The yellow solution was concentrated in vacuo, and purified by flash column chromatography.
-
-
-
|