E. Mash, J. B. Arterburn, S. K. Nimkar
Jun 1, 1992
Citations
0
Influential Citations
2
Citations
Journal
Journal of Carbohydrate Chemistry
Abstract
Abstract A synthesis of (S)-l-phenyl-2-(tert-butyldiphenylsilyloxy)ethyl (2R, 4R. 6S 4-tert-butyldiphenylsilyloxy-6-hydroxymethyl-3, 4, 5, 6-tetrahydro-2H-pyran-2-yl ether, a potentially valuable precursor to the mevinic acid lactone, is described. The synthesis begins with commercially available racemic sodio-3, 4-dihydro-2H-pyran-2-carboxylate and utilizes a chromatographic resolution of diastereomeric (S)-methyl mandelyl; pyranosides and a directed epoxidation. The overall yield, 21% over 10 steps. is competitive with routes from carbohydrates to comparable mevinic acid lactone precursors.