Ammonium Chloride → (3R,4S,5S,6R)-3,4,5-Trisbenzyloxy-6-benzyloxymethyl-2-[3-(5-fluorobenzo[b]thiophen-2-ylmethyl)naphthalen-1-yl]tetrahydropyran-2-ol

HRID 550236

Reaktionsgleichung

Reaktionsgleichung von HRID 550236
CCCCCC.C([Li])CCC.Br[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]([CH2:23][C:24]2[S:28][C:27]3[CH:29]=[CH:30][C:31]([F:33])=[CH:32][C:26]=3[CH:25]=2)[CH:14]=1.[CH2:34]([O:41][CH:42]1[CH:47]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH:46]([O:56][CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[CH:45]([CH2:64][O:65][CH2:66][C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)[O:44][C:43]1=[O:73])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[Cl-].[NH4+]>C1COCC1>[CH2:34]([O:41][C@@H:42]1[C@@H:47]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C@@H:46]([O:56][CH2:57][C:58]2[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=2)[C@@H:45]([CH2:64][O:65][CH2:66][C:67]2[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=2)[O:44][C:43]1([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]([CH2:23][C:24]2[S:28][C:27]3[CH:29]=[CH:30][C:31]([F:33])=[CH:32][C:26]=3[CH:25]=2)[CH:14]=1)[OH:73])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 45855083,4,5-Tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-oneHCID 671565772-(4-Bromonaphthalen-2-ylmethyl)-5-fluorobenzo[b]thiopheneHCID 178418244HCID 178418244, Verbindung

Produkt 1

HCID 67157437(3R,4S,5S,6R)-3,4,5-Trisbenzyloxy-6-benzyloxymethyl-2-[3-(5-fluorobenzo[b]thiophen-2-ylmethyl)naphthalen-1-yl]tetrahydropyran-2-olAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

In a nitrogen stream, an n-butyllithium hexane solution (1.6 M, 0.97 ml, 1.55 mmol) was added dropwise to a solution of 2-(4-bromonaphthalen-2-yl-methyl)-5-fluorobenzo[b]thiophene (520 mg, 1.41 mmol) in THF (15 ml) at −78° C. and the reaction mixture was stirred at the same temperature for 10 minutes. To this solution, a solution of 3,4,5-trisbenzyloxy-6-benzyloxymethyl-tetrahydropyran-2-one (835 mg, 1.55 mmol) in THF (3 ml) was added dropwise. The mixture was stirred at −78° C. for one hour, and a saturated ammonium chloride aqueous solution was added thereto to stop the reaction. The reaction mixture was extracted with ether, and the organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:20)] to obtain the title compound (770 mg, 66%).

Aufarbeitung

  1. stirringThe mixture was stirred at −78° C. for one hour
  2. customthe reaction
  3. extractionThe reaction mixture was extracted with ether
  4. washthe organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. distillationthe solvent was distilled under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:20)]

Quellen und Nachweise

ORD-Eintrag
ord-e1fcc83317c5462b99a40d19af15ac35
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943748B2

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