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0001589756
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The crystallinity of 10 provided the occasion to ensure pure material free of the isomer 9 as well as any unnatural enantiomer (recrystallization, EtOAc-hexane) was enlisted in the subsequent steps
-
Roush, W. R.; Adam, M. A. J. Org. Chem. 1985, 50, 3752. The crystallinity of 10 provided the occasion to ensure pure material free of the isomer 9 as well as any unnatural enantiomer (recrystallization, EtOAc-hexane) was enlisted in the subsequent steps.
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0345350248
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note
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EDCI = 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; HOAt = 1-hydroxy-7-azabenzotriazole; DCC = 1,3-dicyclohexylcarbodiimide.
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38
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0344056652
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note
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16-18 gave the diol (12-42%), and variable amounts of the mono OTBS product (10-28%) and an elimination product (37-65%) derived from loss of one of the L-Htp hydroxy groups.
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39
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0345350247
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note
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2O 3/1/1, 23°C, 10 h (70%).
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42
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0344918997
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Altering the length of time exposed to the hydrolysis conditions alters the relative amounts of 1-3 obtained
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Altering the length of time exposed to the hydrolysis conditions alters the relative amounts of 1-3 obtained.
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