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Enantioselective Chemoenzymatic Synthesis of the S-Enantiomer of the Systemic Fungicide Fenpropimorph (CROSBI ID 113902)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Avdagić, Amir ; Gelo-Pujić, Mirjana ; Šunjić, Vitomir Enantioselective Chemoenzymatic Synthesis of the S-Enantiomer of the Systemic Fungicide Fenpropimorph // Synthesis, 11 (1995), 1427-1431-x

Podaci o odgovornosti

Avdagić, Amir ; Gelo-Pujić, Mirjana ; Šunjić, Vitomir

engleski

Enantioselective Chemoenzymatic Synthesis of the S-Enantiomer of the Systemic Fungicide Fenpropimorph

Chemoenzymatic synthesis of the S-(-)-enantiomer of fenpropimorph (S)-1 in high optical and chemical purity is described. One feature of this process entails the enantioselective acetylation of prochiral 1, 3-propanediol 4 by Pseudomonas sp. lipases, and subsequent transformation of the monoacetate (R)-5 into the final product by the selected order of transformations that comprise ; chlorination or tosylation under non-racemizing conditions, hydrogenolysis of the resulting chloromethyl or tosyl group in (+)-6 and (+)-8, second chlorination of(-)-9, and alkylation of cis-3, 5-dimethylmorpholine by 1-chloropropane derivative (+)-10. This sequence of reactions affords (S)-1, the more active enantiomer in the commercialized racemic mixture with systemic fungicidal activity.

Pseudomonas sp. lipase; monoacetilation; fenpropimorph

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Podaci o izdanju

11

1995.

1427-1431-x

objavljeno

0039-7881

Povezanost rada

Kemija

Indeksiranost