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note
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The oxacarbenium in these reactions likely arises from the 1,2-anhydroseptanose intermediate. A methyl β-septanoside that was subjected to the reaction conditions did not anomerize to the methyl α-septanoside. See the Supplementary data for details.
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12
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74049114682
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note
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The Supplementary data contains MS values for the hydrolysis products.
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15
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0007003020
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1H NMR spectra from which kinetics data were obtained. See also:
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The Supplementary data contains kinetics traces.
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20
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74049149993
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note
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Methyl α-septanoside 14 shares common stereochemistry at C2(3), C(4), C5(6) (septanose numbering) with 23 and they are therefore considered counterparts here. Similarly, 15 is linked to 24 and 16 to 25.
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21
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0002174114
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