4-[(tert-Butyldimethylsilyl)oxy]-6-methoxy-7-methyl-5-(oxiran-2-ylmethyl)-2-benzofuran-3(1H)-one

Abstract

The title compound, C19H28O5Si, was obtained in the reaction of 1,3-dihydro-4-[(tert-butyl­dimethyl­sil­yl)­oxy]-6-meth­oxy-7-methyl-3-oxo-5-(prop-2-en­yl)isobenzofuran with meta-chloro­perbenzoic acid. This reaction is one of the stages of the total synthesis of mycophenolic acid, which we attempted to modify. The title compound forms crystals with only weak inter­molecular inter­actions. The strongest stacking inter­action is found between the benzene and furan rings of inversion-related mol­ecules with a distance of 3.8773 (13) Å between the ring centroids.

Modifications of total synthesis of mycophenolic acid

“…The detailed characteristics of epoxide 4 were reported by our research group previously and its X-ray structure was also determined. 30 The cleavage of 1,2-diols to aldehydes or ketones with periodic acid is a widely used reaction, 29,31 however it was demonstrated, that oxidation of epoxides does not have to proceed through respective diols. 32 In case of epoxide 4, a possible periodate complex might not be formed since the steric hindrance from near methoxyl and TBDMS (t-BuMe2Si-) substituents.…”