Reaktion #790868

ord-7429671ce99340b599e8aab58d7cdd4b

Reaktionsgleichung

CCCCCCCCCCC[C@@H]1C[C@H](O)[C@H](CCCCCC)C(=O)O1
(3S,4S,6R)-tetrahydro-3-hexyl-4-hydroxy-6-undecyl-2H-pyran-2-one
CC(C)(C)[Si](C)(C)Cl
t-butyldimethylchlorosilane
CCOCC
ether
→
CCCCCCCCCCC[C@@H]1C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCCCC)C(=O)O1
(3S,4S,6R)-tetrahydro-3-hexyl -4-[(t-butyldimethylsilyl)oxy-]6-undecyl-2H-pyran-2-one
Ausbeute 63.5%

Edukte

CCCCCCCCCCC[C@@H]1C[C@H](O)[C@H](CCCCCC)C(=O)O1
(3S,4S,6R)-tetrahydro-3-hexyl-4-hydroxy-6-undecyl-2H-pyran-2-one
CC(C)(C)[Si](C)(C)Cl
t-butyldimethylchlorosilane
CCOCC
ether

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
DMF
CN(C)C=O
DMF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Waschenwashed with 1N hydrochloric acid
  2. 2
    SonstigeThe organic phase is dried
  3. 3
    Filtrationfiltered
  4. 4
    Sonstigeevaporated
  5. 5
    SonstigeThe material obtained
  6. 6
    Sonstigeis chromatographed on silica gel

Vorschrift

(1.O.d) 1.5 g of (3S,4S,6R)-tetrahydro-3-hexyl-4-hydroxy-6-undecyl-2H-pyran-2-one are dissolved in 8 ml of DMF. 0.85 g of t-butyldimethylchlorosilane in 4 ml of DMF are then added dropwise. The mixture is stirred for 48 hours. The reaction mixture is poured into 100 ml of ether and washed with 1N hydrochloric acid. The organic phase is dried, filtered and evaporated. The material obtained is chromatographed on silica gel. There are obtained 1.26 g of (3S,4S,6R)-tetrahydro-3-hexyl -4-[(t-butyldimethylsilyl)oxy-]6-undecyl-2H-pyran-2-one, MS: 411 (M+ -t-buytl),

Quelle

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