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Caputo, R.1
Guaragna, A.2
Palumbo, G.3
Pedatella, S.4
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75
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77952993024
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1H NMR analysis of the crude residue)
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1H NMR analysis of the crude residue).
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76
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33748632563
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Stereoelectronic preference for dihydroxylation anti to an allylic hydroxyl group has been recognized previously; see
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Stereoelectronic preference for dihydroxylation anti to an allylic hydroxyl group has been recognized previously; see: Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron 1984, 40, 2247-2255
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(1984)
Tetrahedron
, vol.40
, pp. 2247-2255
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Cha, J.K.1
Christ, W.J.2
Kishi, Y.3
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77
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0035996259
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Hodgston, R.; Majid, T.; Nelson, A. J. Chem. Soc., Perkin Trans.1 2002, 1444-1454
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(2002)
J. Chem. Soc., Perkin Trans.1
, pp. 1444-1454
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Hodgston, R.1
Majid, T.2
Nelson, A.3
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78
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0343526339
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contrast to previous results reported on similar substrates, no traces of the corresponding gulose isomer was herein detected
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In contrast to previous results reported on similar substrates (Harris, J. M.; Keränen, M. D.; Nguyen, H.; Young, V. G.; ODoherty, G. A. Carbohydr. Res. 2000, 328, 17-36) no traces of the corresponding gulose isomer was herein detected
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(2000)
Carbohydr. Res.
, vol.328
, pp. 17-36
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Harris, J.M.1
Keränen, M.D.2
Nguyen, H.3
Young, V.G.4
Odoherty, G.A.5
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79
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0037111592
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Donohoe, T. J.; Blades, K.; Moore, P. R.; Waring, M. J.; Winter, J. J. G.; Helliwell, M.; Newcombe, N. J.; Stemp, G. J. Org. Chem. 2002, 67, 7946-7956
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(2002)
J. Org. Chem.
, vol.67
, pp. 7946-7956
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Donohoe, T.J.1
Blades, K.2
Moore, P.R.3
Waring, M.J.4
Winter, J.J.G.5
Helliwell, M.6
Newcombe, N.J.7
Stemp, G.8
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80
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77952967469
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4); however, only C6 O -deacetylation occurred, even after prolonged reaction times
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4); however, only C6 O -deacetylation occurred, even after prolonged reaction times.
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81
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1642409297
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Use of 1,6-anhydrosugars has been widely applied to the construction of rare sugars and oligosaccharides; see for example
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Use of 1,6-anhydrosugars has been widely applied to the construction of rare sugars and oligosaccharides; see for example: Kulkarni, S. S.; Lee, J.-C.; Hung, S.-C. Curr. Org. Chem. 2004, 8, 475-509
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(2004)
Curr. Org. Chem.
, vol.8
, pp. 475-509
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Kulkarni, S.S.1
Lee, J.-C.2
Hung, S.-C.3
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82
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77952983345
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note
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Solvent substitution (acetone in place of THF) associated with a low temperature (0 °C) was necessary to partially deactivate the reagent, with the aim to prevent formation of 32. Stronger reduction conditions yielded 32 in high yield (see Experimental Section for details).
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83
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77952985247
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note
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It should be mentioned that very prolonged times were required to complete ring opening of 29, as the C3 position was greatly hindered by both the C4 benzyl group and the C1-C6 bridge.
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