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Tetrahydrofuran → N-Acetyl dihydrosphingosine

HRID 222838
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 222838
C1COCC1.[BH4-].[Na+].[C:8]([NH:11][C@H:12]([C@H:18]([OH:34])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[C:13](OCC)=[O:14])(=[O:10])[CH3:9].C(OCC)(=O)C>O>[C:8]([NH:11][C@H:12]([C@H:18]([OH:34])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:13][OH:14])(=[O:10])[CH3:9]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 86638486HCID 86638486, Verbindung

Produkt 1

HCID 6610273N-Acetyl dihydrosphingosineAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A THF suspension (0.3 mL) containing sodium borohydride (38.2 mg, 0.93 mmol) was heated to 60° C., and a THF solution (2.5 mL) of ethyl (2R,3R)-2-acetylamino-3-hydroxyoctadecanoate (250.1 mg. 0.62 mmol) synthesized in the same manner as Example 14 was added thereto dropwise for 5.5 hours. After completion of the dropwise addition, the mixture was further stirred at 60° C. for 17 hours. After ethyl acetate and water were added thereto, the reaction mixture was stirred at 60° C. for 1 hour. After the organic layer was separated, the organic layer was washed with saturated brine and dried with magnesium sulfate. The solvent was removed in reduced pressure. It was confirmed that 178.7 mg of the title compound was contained (yield: 84%). HPLC analysis was carried out to find that the optical purity of the anti-form was 99% ee.

Aufarbeitung

  1. additionwas added
  2. additionAfter completion of the dropwise addition
  3. stirringthe reaction mixture was stirred at 60° C. for 1 hour
  4. customAfter the organic layer was separated
  5. washthe organic layer was washed with saturated brine
  6. dry with materialdried with magnesium sulfate
  7. customThe solvent was removed in reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f2baead9609d4f84b39619e6d1d61a41
Quelldatensatz
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08207370B2

Notizen zur Reaktion

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