Reaktion #309118

Reaktionsgleichung

(1S,3′R,4′S,5′S,6′R)-3′,4′,5′-tris-benzyloxy-6′-benzyloxymethyl-8-[(4-ethylphenyl)methyl]-3,3′,4,4′,5′,6′-hexahydro-spiro[2-oxa-9-thia-fluorene-1,2′-[2H]pyran]

→

titled compound

Ausbeute 81.4%

(1S,3′R,4′S,5′S,6′R)-8-[(4-ethylphenyl)methyl]-3,3′,4,4′,5′,6′-hexahydro-6′-hydroxymethyl-spiro[2-oxa-9-thia-fluorene-1,2′-[2H]pyran]-3′,4′,5′-triol

Ausbeute 81.4%

Lösungsmittel

methanol

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe catalyst was then filtered off
2. 2
   SonstigeSolvent was then removed by distillation under reduced pressure
3. 3
   Sonstigethe resulting residue was purified by silica gel column chromatography (developing solution=dichloromethane:methanol (10:1))

Vorschrift

To a solution of (1S,3′R,4′S,5′S,6′R)-3′,4′,5′-tris-benzyloxy-6′-benzyloxymethyl-8-[(4-ethylphenyl)methyl]-3,3′,4,4′,5′,6′-hexahydro-spiro[2-oxa-9-thia-fluorene-1,2′-[2H]pyran] (23 mg, 0.028 mmol) in methanol (1 mL) and ethyl acetate (1 mL) was added 10% palladium on carbon (10 mg). The resultant mixture was stirred under a hydrogen atmosphere for 1 hour at room temperature, and the catalyst was then filtered off. Solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solution=dichloromethane:methanol (10:1)), to thereby obtain the titled compound (10.4 mg, 81%).

Quelle