Tetrabutylammonium Fluoride → (4R,6R)-6-([1S,2S,6S,8S,8aR]-2-{1,2,6,7,8,8a-Hexahydro-6-hydroxy-8-[(2RS)-2-(2-acetylphenoxy)butyryloxy]-2-methyl-1-naphthyl}ethyl)tetrahydro-4-hydroxy-2H-pyran-2-one

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Reaction Steps

A procedure similar to that described in Example 2, above, was followed, but using 1.11 g of (4R,6R)-6-([1S,2S,6S,8S,8aR]-2-{1,2,6,7,8,8a-hexahydro-6-t-butyldimethylsilyloxy-8-[(2RS)-2-(2-acetylphenoxy)butyryloxy]-2-methyl-1-naphthyl}ethyl)tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one [prepared as described inExample 97, above] and 35.3 ml of a 1.0 molar solution of tetrabutylammonium fluoride in tetrahydrofuran, to give 0.34 g of the title compound as white crystals, melting at between 148° and 150° C. Nuclear Magnetic Resonance Spectrum (270 MHz CDCl3) δ ppm: 1.10 (3H, triplet, J=7.3 Hz); 2.62 (3H, singlet); 4.32-4.52 (3H, multiplet); 4.81 (1H, triplet, J=5.9 Hz); 5.44 (1H, broad singlet); 5.52 (1H, broad singlet); 5.82 (1H, doublet of doublets, J=5.9 & 9.9 Hz); 5.93 (1H, doublet, J=9.9 Hz); 6.88 (1H, doublet, J=7.9 Hz); 7.00 (1H, triplet, J=8.6 Hz); 7.41 (1H, triplet, J=8.6 Hz); 7.72 (1H, doublet, J=7.9Hz).

Provenance & Evidence