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10044234778
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D +26 (c 1.0, MeOH) [lit. +26 (c 1.0, MeOH, Sigma-Aldrich)].
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37
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10044282427
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note
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Compound 11 was epimerized at the stereogenic center corresponding to Cα in hydroxylysine by treatment with NaHMDS (1 equiv) in THF. Analysis of the diasteromeric mixture by reversed-phase HPLC displayed two peaks having identical mass spectra. Only one of the two diastereomers was detected by HPLC when 11 was prepared by alkylation of 16b with 10.
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38
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0034682173
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10044256109
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note
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Two equivalents of sodium cyanoborohydride and tert-butyldimethyl silyl chloride was used with acetonitrile as solvent at room temperature.
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42
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10044245665
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note
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1H NMR shift of ∼1.15 ppm for the proximal hydrogen atom. As expected acetylation of the primary hydroxyl group in 20a/b caused a smaller shift (∼0.35 ppm) of the adjacent hydrogen atoms. The identity and the yields for compounds 22a/b, 23a/b, 26a/b, and 27a/b obtained after reductive opening of 21 and 25 were determined in the same manner.
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43
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10044250772
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note
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13C NMR data.
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