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1
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16044375035
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note
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(a) For a compilation of references to recent advances in this area, see footnote 2b.
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3
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0028122946
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(a) Crich, D.; Brunckova, J.; Yao, Q. Tetrahedron Lett. 1994, 35, 6619.
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Crich, D.1
Brunckova, J.2
Yao, Q.3
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4
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0030027050
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(b) Crich, D.; Sun, S.; Brunckova, J. J. Org. Chem. 1996, 61, 605.
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Crich, D.1
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5
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0000584917
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(c) Dan, A.; Ito, Y.; Ogawa, T. J. Org. Chem. 1995, 60, 4680.
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Dan, A.1
Ito, Y.2
Ogawa, T.3
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6
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0028065448
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Yamazaki, N.; Eichenberger, E. Curran, D. P. Tetrahedron Lett. 1994, 35, 6623.
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Tetrahedron Lett.
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Yamazaki, N.1
Eichenberger, E.2
Curran, D.P.3
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7
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33847798596
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-
Axial quenching of 1-alkoxy-1-glycosyl radicals was initially predictable in so far as it is effectively the microscopic reverse of hydrogen atom abstraction from alkoxytetrahydropyrans by electrophilic radicals wherein the axial hydrogen is abstracted up to eight times as rapidly as the equatorial one: (a) Hayday, K.; McKelvey, R. D. J. Org. Chem. 1976, 41, 2222. (b) Beckwith, A. L. J.; Easton, C. J. J. Am. Chem. Soc. 1981, 103, 615. (c) Beckwith, A. L. J.; Brumby, S. J. Chem. Soc., Perkin Trans. 2 1987, 1801.
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J. Org. Chem.
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Hayday, K.1
McKelvey, R.D.2
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8
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0000516387
-
-
Axial quenching of 1-alkoxy-1-glycosyl radicals was initially predictable in so far as it is effectively the microscopic reverse of hydrogen atom abstraction from alkoxytetrahydropyrans by electrophilic radicals wherein the axial hydrogen is abstracted up to eight times as rapidly as the equatorial one: (a) Hayday, K.; McKelvey, R. D. J. Org. Chem. 1976, 41, 2222. (b) Beckwith, A. L. J.; Easton, C. J. J. Am. Chem. Soc. 1981, 103, 615. (c) Beckwith, A. L. J.; Brumby, S. J. Chem. Soc., Perkin Trans. 2 1987, 1801.
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J. Am. Chem. Soc.
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Beckwith, A.L.J.1
Easton, C.J.2
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9
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37049080023
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-
Axial quenching of 1-alkoxy-1-glycosyl radicals was initially predictable in so far as it is effectively the microscopic reverse of hydrogen atom abstraction from alkoxytetrahydropyrans by electrophilic radicals wherein the axial hydrogen is abstracted up to eight times as rapidly as the equatorial one: (a) Hayday, K.; McKelvey, R. D. J. Org. Chem. 1976, 41, 2222. (b) Beckwith, A. L. J.; Easton, C. J. J. Am. Chem. Soc. 1981, 103, 615. (c) Beckwith, A. L. J.; Brumby, S. J. Chem. Soc., Perkin Trans. 2 1987, 1801.
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J. Chem. Soc., Perkin Trans. 2
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Beckwith, A.L.J.1
Brumby, S.2
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10
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0007819572
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(a) Malatesta, V.; McKelvey, R. D.; Babcock, B. W.; Ingold, K. U. J. Org. Chem., 1979, 44, 1872.
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Malatesta, V.1
McKelvey, R.D.2
Babcock, B.W.3
Ingold, K.U.4
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13
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11644264856
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Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901.
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Barton, D.H.R.1
Crich, D.2
Motherwell, W.B.3
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24
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0001651721
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Also see: (a) Kahne, D.; Yang, D.; Lim, J. J.; Miller, R.; Paguaga, E. J. Am. Chem. Soc. 1988, 110, 8716. (b) Sugai, T.; Shen, G.-J.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 413.
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Kahne, D.1
Yang, D.2
Lim, J.J.3
Miller, R.4
Paguaga, E.5
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25
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0000984816
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-
Also see: (a) Kahne, D.; Yang, D.; Lim, J. J.; Miller, R.; Paguaga, E. J. Am. Chem. Soc. 1988, 110, 8716. (b) Sugai, T.; Shen, G.-J.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 413.
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Sugai, T.1
Shen, G.-J.2
Ichikawa, Y.3
Wong, C.-H.4
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28
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0000331272
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(c) However, for recent advances, see: Martichonok, V.; Whitesides, G. M. J. Org. Chem. 1996, 61, 1702.
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Martichonok, V.1
Whitesides, G.M.2
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(a) Danishefsky, S. J.; Pearson, W. H.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 1280.
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(b) DeNinno, M. P., Danishefsky, S. J.; Schulte, G. J. Am. Chem. Soc. 1988, 110, 3925.
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0023889181
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(c) Danishefsky, S. J.; DeNinno, M. P.; Chen, S.-H. J. Am. Chem. Soc. 1988, 110, 3929.
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Danishefsky, S.J.1
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Chen, S.-H.3
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0040725523
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Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3986.
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Carlsen, P.H.J.1
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Martin, V.S.3
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33
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0027367150
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Dondoni, A.; Marra, A.; Scherrmann, M.-C. Tetrahedron Lett. 1993, 34, 7323.
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Dondoni, A.1
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0027997412
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Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
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Ley, S.V.1
Norman, J.2
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Marsden, S.P.4
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Huang, S.-L.2
Swern, D.3
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40
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0345529661
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For previous examples of the oxidation of substituted furans to 1,2-dicarbonyl compounds, see: (a) White, H. M.; Colomb, H. O.; Bailey, P. S. J. Org. Chem. 1965, 30, 481. (b) Bailey, P. S.; White, H. M.; Colomb, H. O. J. Org. Chem. 1965, 30, 487.
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White, H.M.1
Colomb, H.O.2
Bailey, P.S.3
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41
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16044373991
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For previous examples of the oxidation of substituted furans to 1,2-dicarbonyl compounds, see: (a) White, H. M.; Colomb, H. O.; Bailey, P. S. J. Org. Chem. 1965, 30, 481. (b) Bailey, P. S.; White, H. M.; Colomb, H. O. J. Org. Chem. 1965, 30, 487.
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(b) Atwal, K. S.; Sahoo, S. P.; Tsai, T. Y. R.; Wiesner, K. Heterocycles 1982, 19, 641.
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Atwal, K.S.1
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Tsai, T.Y.R.3
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16044369967
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Bandzouzi, A.; Lakhrissi, M.; Chapleur, Y. J. Chem. Soc., Perkin Trans. 1 1992, 147.
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Bandzouzi, A.1
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Chapleur, Y.3
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49
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16044366551
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note
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Interestingly, this strain is mainly due to the 4,6-, rather than the 2,3-acetonide, as subsequent experiments with 4,6-O-isopropylidene-2,3-di-O-[[2-(trimethylsilyl)ethoxy]methyI]mannonolactone gave exactly analogous results.
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51
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0003405157
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Georg Thieme Verlag: Stuttgart
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Reviews: (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; 2nd ed.; Wiley, New York, 1991. (b) Kocienski, P. J. Protecting Groups; Georg Thieme Verlag: Stuttgart, 1994.
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Protecting Groups
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(a) Lipshutz, B. H.; Pegram, J. J.; Morey, M. C. Tetrahedron Lett. 1981, 22, 4603.
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3RhCl/BuLi couple, see: Boons, G.-J.; Burton, A.; Isles, S. J. Chem. Soc., Chem. Commun. 1996, 141.
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84988116166
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(b) Oltvoort, J. J.; van Boeckel, C. A. A.; de Konig, J. H.; van Boom, J. H. Synthesis 1981, 305.
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67
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0026500414
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Attempted application of this exchange process to the glycosyl donor 28 failed, probably due to poisoning of the catalysts by the thiol ether moiety: Yin, H.; Franck. R. W.; Cheng, S.-L.; Quigley, G. J.; Todaro, L. J. Org. Chem. 1992, 57, 644.
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72
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16044365256
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note
-
Owing to insufficient spectral resolution, it is unclear whether this isomer differs from 4 in anomeric configuration or is the result of a manno- to gluco-isomerization.
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74
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33845554860
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(a) Lewis, M. D.; Cha, J.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976.
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