Reaktion #790870

ord-baff25b0475d49fbadb8b34376703cfc

Reaktionsgleichung

CCCCCCCCCCC[C@H](C[C@H](O)[C@H](CCCCCC)C(=O)OCc1ccccc1)OC1CCCCO1
benzyl (2S 3S,5R)-2-hexyl-3-hydroxy-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoate
→
CCCCCCCCCCC[C@H](C[C@H](O)[C@H](CCCCCC)C(=O)O)OC1CCCCO1
(2S,3S,5R)-2-hexyl-3-hydroxy-5-[(tetrahydro-2H -pyran-2-yl)oxy]hexadecanoic acid

Edukte

CCCCCCCCCCC[C@H](C[C@H](O)[C@H](CCCCCC)C(=O)OCc1ccccc1)OC1CCCCO1
benzyl (2S 3S,5R)-2-hexyl-3-hydroxy-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoate

Reagenzien

[Pd]
Pd/C

Lösungsmittel

C1CCOC1
THF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe catalyst is filtered off
  2. 2
    Sonstigeafter evaporation of the filtrate
  3. 3
    Sonstigethe crude product is chromatographed on silica gel

Vorschrift

(1.O.h) 430 mg of benzyl (2S 3S,5R)-2-hexyl-3-hydroxy-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoate in 10 ml of THF are treated with Pd/C 10% and hydrogenated for 3 hours. The catalyst is filtered off and, after evaporation of the filtrate, the crude product is chromatographed on silica gel. There is obtained (2S,3S,5R)-2-hexyl-3-hydroxy-5-[(tetrahydro-2H -pyran-2-yl)oxy]hexadecanoic acid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04983746uspto-grants-1991_01