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(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → tert-Butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate

HRID 993418
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 993418
[Cl:1][CH2:2][C@@H:3]([OH:15])[CH2:4][C:5](=[O:14])[CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O>P([O-])([O-])([O-])=O>[Cl:1][CH2:2][C@@H:3]([OH:15])[CH2:4][C@@H:5]([OH:14])[CH2:6][C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 7022053tert-butyl (5S)-6-chloro-5-hydroxy-3-oxohexanoate

Produkt 1

HCID 9816157tert-Butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1061PhosphateLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

Large-sized test tubes were charged with 7 mL of said medium B and, after sterilization, inoculated with the bacteria shown in Table 2, respectively. Then, aerobic shake culture was carried out at 30° C. for 1 day. From the resulting culture broth, the cells were harvested by centrifugation and suspended in 0.5 mL of 50 mM phosphate buffer (pH 6.5) containing 0.5% of tert-butyl(5S)-6-chloro-5-hydroxy-3-oxohexanoate and 1.5% of glucose. The suspension was placed in a 10 mL test tube equipped with a stopper and the reaction was carried out under shaking at 30° C. for 20 hours. After completion of the reaction, the reaction mixture was extracted with 0.5 mL of ethyl acetate and the ethyl acetate phase was analyzed by high performance liquid chromatography (column: Nakalai-Tesque's Cosmocil 5CN-R (4.6 mm×250 mm), eluent: 1 mM phosphoric acid/H2O:acetonitrile=5:1, flow rate: 0.7 mL/min., detection: at 210 nm, column temperature: 30° C.) for reaction rate and for the diastereomer ratio of the product tert-butyl(3R,5S)-6-chloro-3,5-dihydroxyhexanoate. The results are shown in Table 2.

Aufarbeitung

  1. additionLarge-sized test tubes were charged with 7 mL of said medium B
  2. customThe suspension was placed in a 10 mL test tube
  3. customequipped with a stopper
  4. customAfter completion of the reaction
  5. extractionthe reaction mixture was extracted with 0.5 mL of ethyl acetate
  6. customthe ethyl acetate phase was analyzed by high performance liquid chromatography (column: Nakalai-Tesque's Cosmocil 5CN-R (4.6 mm×250 mm), eluent: 1 mM phosphoric acid/H2O:acetonitrile=5:1, flow rate: 0.7 mL/min., detection: at 210 nm, column temperature: 30° C.) for reaction rate and for the diastereomer ratio of the product tert-butyl(3R,5S)-6-chloro-3,5-dihydroxyhexanoate

Quellen und Nachweise

ORD-Eintrag
ord-e8499c536af14efa9097fe5382214da5
Quelldatensatz
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06472544B1

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