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As the information concerning the relationship of the b-selectivity of mannosylation and the addition rate of the mannosyl donor (see references [17d] and [25]) is not available, the donor addition rate reported in the literature[17d] (0.25m of mannosyl donor was added over a period of 25 min) was used as a reference in this study
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N-(b-Mannopyranosyl)trichloroacetamide 5 was isolated and the anomeric configuration was evidenced by the 13C NMR spectroscopic chemical shift at d=79.4 ppm and the 1JCH coupling constant of 161 Hz (see the Experimental Section)
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N-(b-Mannopyranosyl) trichloroacetamide 5 was isolated and the anomeric configuration was evidenced by the 13C NMR spectroscopic chemical shift at d=79.4 ppm and the 1JCH coupling constant of 161 Hz (see the Experimental Section).
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During the revision of this manuscript, one of the referees recommended this study to use the mannosyl N-phenyltrifluoroacetimidate donor for the elimination the formation of the amide byproduct (5) (see references [17h], [17i], and [17l]). However, the preparation of this imidate donor requires the use of unstable N-phenyl trifluoroacetimidoyl chloride, which has not been realized in our hands. For the preparation of acetimidoyl chlorides
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synthesis of methyl 2,3,6-tri-O-benzyl b-d-glucopyranoside 7
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b) synthesis of methyl 2,3,6-tri-O-benzyl b-d-glucopyranoside 7: M. P. DeNinno, J. B. Etienne, K. C. Duplantier, Tetrahedron Lett. 1995, 36, 669-672;
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Deninno, M.P.1
Etienne, J.B.2
Duplantier, K.C.3
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83
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77951812726
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diisopropylidene galactopyranose 8 is commercially available
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c) diisopropylidene galactopyranose 8 is commercially available;
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-
-
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84
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35349005706
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synthesis of methyl 2,3,4-tri-O-benzyl b-d-glucopyranoside 9
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d) synthesis of methyl 2,3,4-tri-O-benzyl b-d-glucopyranoside 9: C.-R. Shie, Z.-H. Tzeng, S. S. Kulkarni, B.-J. Uang, C.-Y. Hsu, S.-C. Hung, Angew. Chem. 2005, 117, 1693-1696;
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Angew. Chem.
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Shie, C.-R.1
Tzeng, Z.-H.2
Kulkarni, S.S.3
Uang, B.-J.4
Hsu, C.-Y.5
Hung, S.-C.6
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85
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17044368829
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Angew. Chem. Int. Ed. 2005, 44, 1665-1668.
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(2005)
Angew. Chem. Int. Ed.
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, pp. 1665-1668
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93
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64349084051
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E. A. Mensah, J. M. Azzarelli, H. M. Nguyen, J. Org. Chem. 2009, 74, 1650-1657.
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J. Org. Chem.
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Mensah, E.A.1
Azzarelli, J.M.2
Nguyen, H.M.3
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94
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77951770262
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This explanantion was suggested by one of the referees in the revision of this manuscript, whereas in our perspective, we do not exclude other possible causes unless further experimental evidence is obtained
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This explanantion was suggested by one of the referees in the revision of this manuscript, whereas in our perspective, we do not exclude other possible causes unless further experimental evidence is obtained.
-
-
-
-
95
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-
0031749791
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-
Syntheses of 13, 14, 16, 17, 23, 24, and 25 were detailed in the Supporting Information. Since synthesis of 15 and 16 employed the same route, only the synthesis of 16 was described in the Supporting Information. For the synthesis of 16
-
Syntheses of 13, 14, 16, 17, 23, 24, and 25 were detailed in the Supporting Information. Since synthesis of 15 and 16 employed the same route, only the synthesis of 16 was described in the Supporting Information. For the synthesis of 16: a) J. Gildersleeve, R. A. Pascal, D. Kahn, J. Am. Chem. Soc. 1998, 120, 5961-5969;
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(1998)
J. Am. Chem. Soc.
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Gildersleeve, J.1
Pascal, R.A.2
Kahn, D.3
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96
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77951771974
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b) A. Irina, A. J. Ivanova, M. A. J. F. Ross, V. N. Andrei, J. Chem. Soc. Perkin Trans. 1 1999, 1743-1753;
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(1999)
J. Chem. Soc. Perkin Trans.
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, pp. 1743-1753
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Irina, A.1
Ivanova, A.J.2
Ross, M.A.J.F.3
Andrei, V.N.4
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97
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70350233347
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for the synthesis of 23
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c) for the synthesis of 23: C.-S. Chao, C.-W. Li, M.-C. Chen, S.-S. Chang, K.-K. T. Mong, Chem. Eur. J. 2009, 15, 10972-10982.
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(2009)
Chem. Eur. J.
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, pp. 10972-10982
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Chao, C.-S.1
Li, C.-W.2
Chen, M.-C.3
Chang, S.-S.4
Mong, K.-K.T.5
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100
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0002031888
-
-
a) N. K. Kochetkov, B. A. Dmitriev, O. S. Chizhov, E. M. Klimov, N. N. Malysheva, A. Y. Chernyak, N. E. Bayramova, V. I. Torgov, Carbohydr. Res. 1974, 33, C5-C7;
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Carbohydr. Res.
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Kochetkov, N.K.1
Dmitriev, B.A.2
Chizhov, O.S.3
Klimov, E.M.4
Malysheva, N.N.5
Chernyak, A.Y.6
Bayramova, N.E.7
Torgov, V.I.8
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101
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0016627258
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b) N. K. Kochetkov, B. A. Dmitriev, O. S. N. N. Malysheva, A. Y. Chernyak, E. M. Klimov, N. E. Bayramova, V. I. Torgov, Carbohydr. Res. 1975, 45, 283-290.
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Kochetkov, N.K.1
Dmitriev, B.A.2
Malysheva, O.S.N.N.3
Chernyak, A.Y.4
Klimov, E.M.5
Bayramova, N.E.6
Torgov, V.I.7
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102
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77951805100
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Synthesis of 28 was described in the Supporting Information
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Synthesis of 28 was described in the Supporting Information.
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-
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105
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7244245511
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Angew. Chem. Int. Ed. 2004, 43, 5386-5389.
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