Reaktion #309117

Reaktionsgleichung

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

4-ethylphenylboronic acid

potassium phosphate

triphenylphosphine

toluene

→

titled compound

Ausbeute 56.3%

(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]

Ausbeute 56.3%

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenSolvent was concentrated under reduced pressure
2. 2
   Sonstigethe resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:3))

Vorschrift

Under a nitrogen stream, to a mixture of (1S,3′R,4′S,5′S,6′R)-3′,4′,5′-tris-benzyloxy-6′-benzyloxymethyl-8-chloromethyl-3,3′,4,4′,5′,6′-hexahydro-spiro[2-oxa-9-thia-fluorene-1,2′-[2H]pyran] (41 mg, 0.05 mmol), 4-ethylphenylboronic acid (13.0 mg, 0.08 mmol), potassium phosphate (21.0 mg, 1.00 mmol), palladium acetate (1.2 mg, 0.005 mmol) and triphenylphosphine (2.6 mg, 0.01 mmol) was added toluene (2.6 mg, 0.5 mmol), and the resultant solution was stirred for 4 hours at 80° C. Solvent was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:3)), to thereby obtain the titled compound (23 mg, 56%).

Quelle