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34047261471
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35
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77955653859
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M. Shiozaki, T. Tashiro, H. Koshino, R. Nakagawa, S. Inoue, T. Shigeura, H. Watarai, M. Taniguchi, and K. Mori Carbohydr. Res. 345 2010 1663
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Shiozaki, M.1
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Taniguchi, M.8
Mori, K.9
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36
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79955674974
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The numbers were assigned based on the starting material fructose
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The numbers were assigned based on the starting material fructose.
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37
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79955660673
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note under CCDC refno. 801190 and 801191, respectively
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3, Z = 4, Mo Kα radiation (λ = 0.71073 ), T = 100(2) K; R1 = 0.0626, wR2 = 0.1556 (I >2σ(I)); R1 = 0.0667, wR2 = 0.1589 (all data). The CIF file for the crystal data of compound 8 and 16 is available from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif under CCDC ref no. 801190 and 801191, respectively.
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38
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79955656656
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Hydrogen atoms were removed for clarity of the structure
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Hydrogen atoms were removed for clarity of the structure.
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39
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0033529819
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A similar kind of intermediate has been found in the azidation of 1,2 and 1,3-diols by azidotrimethylsilane via a Mitsunobu reaction to give C-2 and C-3 azides, respectively. It is also noticed that the selectivity depends on the surrounding sterichindrance of the C-2 or C-3 alcohol. L. He, M. Wanunu, H.-S. Byun, and R. Bittmann J. Org. Chem. 64 1999 6049
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He, L.1
Wanunu, M.2
Byun, H.-S.3
Bittmann, R.4
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41
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79955650191
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note
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3P and 6a in THF with water. This intermediate was further confirmed by observing a downfield shift of C1 protons in the corresponding C1-O-acetylated derivative. Where as a downfield shift of C2 proton was observed in C2-O-acetylated derivative of compound 6a.
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45
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0035018517
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O.R. Martin, O.M. Saavedra, F. Xie, L. Liu, S. Picasso, P. Vogel, H. Kizu, and N. Asano Bioorg. Med. Chem. 9 2001 1269
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Bioorg. Med. Chem.
, vol.9
, pp. 1269
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Martin, O.R.1
Saavedra, O.M.2
Xie, F.3
Liu, L.4
Picasso, S.5
Vogel, P.6
Kizu, H.7
Asano, N.8
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46
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13844312017
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J.-Y. Goujon, D. Gueyrard, P. Compain, O.R. Martin, K. Ikeda, A. Kato, and N. Asano Bioorg. Med. Chem. 13 2005 2313
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(2005)
Bioorg. Med. Chem.
, vol.13
, pp. 2313
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Goujon, J.-Y.1
Gueyrard, D.2
Compain, P.3
Martin, O.R.4
Ikeda, K.5
Kato, A.6
Asano, N.7
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50
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79955667717
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note
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3P (781.6 mg, 2.98 mmol) and phthalimide (175.3 mg, 1.19 mmol) in dry THF (8 mL) at 0 °C was injected DIAD (602 mg, 2.98 mmol) dropwise. The reaction mixture was allowed to stir at 25 °C for 6 h. After completion of reaction (by TLC) the mixture was concentrated and the product was purified by column chromatography using ethyl acetate: hexane (1:9) to give compound 8 (322 mg, 75%) as a colorless liquid.
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