Reaktion #321430

ord-53d350a606aa49208bf95ac41ea8e1ae

Reaktionsgleichung

CC(=O)O[C@@H]1C2=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)c3ccccc3)c3ccccc3)C[C@@](O)([C@@H](OC(=O)c3ccccc3)[C@@H]3[C@]4(OC(C)=O)CO[C@@H]4C[C@H](O)[C@@]3(C)[C@H]1O)C2(C)C
compound 12
CC(=O)O[C@@H]1C2=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)c3ccccc3)c3ccccc3)C[C@@](O)([C@@H](OC(=O)c3ccccc3)[C@@H]3[C@]4(OC(C)=O)CO[C@@H]4C[C@H](O)[C@@]3(C)[C@H]1O)C2(C)C
9-Dihydrotaxol
→
O=Cc1ccccc1
benzaldehyde
CC(=O)O[C@@H]1C2=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)c3ccccc3)c3ccccc3)C[C@@](O)([C@@H](OC(=O)c3ccccc3)[C@@H]3[C@]4(OC(C)=O)CO[C@@H]4C[C@H](O)[C@@]3(C)[C@H]1O)C2(C)C
9-dihydrotaxol-7,9-benzylidene acetal
CC(=O)O[C@@H]1C2=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)c3ccccc3)c3ccccc3)C[C@@](O)([C@@H](OC(=O)c3ccccc3)[C@@H]3[C@]4(OC(C)=O)CO[C@@H]4C[C@H](O)[C@@]3(C)[C@H]1O)C2(C)C
9-Dihydrotaxol

Edukte

CC(=O)O[C@@H]1C2=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)c3ccccc3)c3ccccc3)C[C@@](O)([C@@H](OC(=O)c3ccccc3)[C@@H]3[C@]4(OC(C)=O)CO[C@@H]4C[C@H](O)[C@@]3(C)[C@H]1O)C2(C)C
compound 12
CC(=O)O[C@@H]1C2=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)c3ccccc3)c3ccccc3)C[C@@](O)([C@@H](OC(=O)c3ccccc3)[C@@H]3[C@]4(OC(C)=O)CO[C@@H]4C[C@H](O)[C@@]3(C)[C@H]1O)C2(C)C
9-Dihydrotaxol
—
product

Reagenzien

Keine

Lösungsmittel

ClCCl
methylene chloride

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

15 mg of the product of Example 8 were treated with 0. 1 ml benzaldehyde in 0.6 ml methylene chloride to give 1.1 mg of 9-dihydrotaxol-7,9-benzylidene acetal (Scheme 3, compound 12, X=H, Y=Ph).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05594157uspto-grants-1997_01