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Crystallographic data (excluding structure factors) for azidoformate 1 and α-isopropyl-2-amido-2-deoxy allopyranoside 2c-α have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 185294 (1) and 185295 (2c-α). These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033; or deposit@ccdc.cam.ac.uk)
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Crystallographic data (excluding structure factors) for azidoformate 1 and α-isopropyl-2-amido-2-deoxy allopyranoside 2c-α have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 185294 (1) and 185295 (2c-α). These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033; or deposit@ccdc.cam.ac.uk).
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24
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84980188341
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Caution! Azidoformates are potentially explosive. We have encountered no difficulties with the preparation and use of azidoformate 1, but appropriate safety precautions are strongly recommended. For instance, since metal salts catalyze their decomposition, it may be wise to avoid using metal spatulas to handle larger quantities of azidoformates. Detonation of a low molecular weight azidoformate during distillation has been reported: Feyen P. Angew. Chem., Int. Ed. 16:1977;115.
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Feyen, P.1
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0010594981
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. For an early approach to an oxazolidinone-protected 2-amino-2-deoxy-D-allopyranoside, see: Miyai K., Zimmerman H.K., Gross P.H. J. Org. Chem. 34:1969;1635-1637.
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0010629488
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1H NMR, IR, and HRMS
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1H NMR, IR, and HRMS.
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27
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0010629489
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2) provided β-ethyl-2-amido allopyranoside 2a-β (12.0 mg, 55%) as a glassy solid
-
2) provided β-ethyl-2-amido allopyranoside 2a-β (12.0 mg, 55%) as a glassy solid.
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28
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0010628488
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36
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0010625146
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C1-H values, 174 and 175 Hz, for 2g-β and 2g-α, respectively
-
C1-H values, 174 and 175 Hz, for 2g-β and 2g-α, respectively.
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-
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37
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0010555946
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2-promoted cases
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2-promoted cases.
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39
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0034609678
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Petillo, P.A.5
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0035963682
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For examples of glycosyl iodides in synthesis, see: (a) Bhat, A. S.; Gervay-Hague, J. Org. Lett. 2001, 3, 2081-2084;
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0001410949
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