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33748893276
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note
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[7a]. For this reason, all erythrulose derivatives prepared subsequently, including the D series, always carried the TBDPS group.
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33748913785
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note
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Erythrulose derivatives are prone to a slow epimerization with the consequent loss of optical purity. We therefore prepared them just prior to use by oxidation of the appropriate precursor.
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33748901705
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note
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One could envisage in principle to perform the same reaction sequences on 8 as the starting material. However, in the course of these reactions C-5 of 7 becomes eventually the carbonyl group of the target L-erythrulose derivative. Consequently, since 7 and 8 only differ in the configuration at C-5, the reaction sequences would afford in both cases L-erythrulose derivatives.
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54
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37049061188
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58
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33748908272
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note
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[14] had to be used here, as the Swern method gave low yields and partial decomposition.
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59
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33748913966
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note
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With the signal-to-noise ratio observed in the NMR measurements, even 1% of the diastereomeric ketone would have been detected.
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