Synthesis of methyl (E)-2-[(3S,4S)-4-hydroxy-3-(pent-3-yloxy)-pyrrolidin-2-ylidene]propanoate and its unusual recyclization |
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| Authors: | F A Gimalova G M Khalikova V A Egorov A G Mustafin M S Miftakhov |
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| Institution: | 1. Institute of Organic Chemistry, Ufa Research Center of the Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation
2. Department of Chemistry, Bashkir State University, 32 ul. Z. Validi, 450074, Ufa, Russian Federation
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| Abstract: | Methyl (2E,4S,5S)-5-hydroxy-6-mesyloxy-2-methyl-4-(pent-3-yloxy)hex-2-enoate was synthesized from l-tartaric acid. Attempted substitution of the mesyloxy group by the reaction with NaN3 directly led to methyl (E)-2-(3S,4S)-4-hydroxy-3-(pent-3-yloxy)pyrrolidin-2-ylidene]propanoate. The latter on treatment with CF3COOH and then NaOH gave methyl (2E)-2-methyl-4-(S)-oxiran-2-yl]-4-(pent-3-yloxy)but-2-enoate. |
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