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One further reference reports the synthesis of tetrahydrolipstatin 3; in this article a 1:1 mixture of diastereoisomers is obtained, although the details of their separation are not included. See:
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One further reference reports the synthesis of tetrahydrolipstatin 3; in this article a 1:1 mixture of diastereoisomers is obtained, although the details of their separation are not included. See:. Parsons P.J., and Cowell J.K. Synlett (2000) 107
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The (R)-α-methylbenzylamine used for derivatisation was determined to be of 99% ee. An analogous reaction was also carried out using racemic β-lactone 13 producing a 50:50 mixture of diastereoisomeric amides, thus confirming that a resolution process was not occurring. For a related example, see:
-
The (R)-α-methylbenzylamine used for derivatisation was determined to be of 99% ee. An analogous reaction was also carried out using racemic β-lactone 13 producing a 50:50 mixture of diastereoisomeric amides, thus confirming that a resolution process was not occurring. For a related example, see:. Giresbeck A., and Seebach D. Helv. Chim. Acta 70 (1987) 1326
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77
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57149090585
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note
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4.
-
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78
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0001222554
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Utaka M., Watabu H., Higashi H., Sakai T., Tsuboi S., and Torii S. J. Org. Chem. 55 (1990) 3917
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83
-
-
57149095330
-
-
note
-
31P NMR spectroscopy which enabled a diastereoisomeric ratio of 96:3:1 to be determined.
-
-
-
-
86
-
-
57149105207
-
-
note
-
An authentic sample of tetrahydrolipstatin 3 was kindly supplied by Dr. M. Karpt and Dr. U. Zutter of Hoffman-La Roche.
-
-
-
-
87
-
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57149097343
-
-
note
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4.
-
-
-
-
88
-
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57149087345
-
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Utaka M., Watabu H., Higashi H., Sakai T., Tsuboi S., and Torii S. J. Org. Chem. 55 (1990) 3817
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J. Org. Chem.
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Utaka, M.1
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Sakai, T.4
Tsuboi, S.5
Torii, S.6
-
89
-
-
57149084759
-
-
note
-
31P NMR spectroscopy; comparison with authentic samples of the minor diastereoisomers (and analogues produced during the synthesis of tetrahydrolipstatin 3) enabled a diastereoisomeric ratio of 93:5:2 to be determined.
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