(±)-((2<i>S</i>,5<i>R</i>)-5-(Acetoxymethyl)tetrahydrofuran-2-yl)methyl Benzoate

Abstract

In this note we report the synthesis of a doubly acylated cis-THF-diol product synthesised in three steps by the stereoselective RuO4-catalysed oxidative cyclisation of 1,5-hexadiene, followed by benzoylation and acetylation. This substance is one of the substrates chosen to probe a new developed oxidative procedure to transform bis-acylated THF-diols into bis-acylated 1,4-diketones. This new derivative was fully characterised by spectroscopic methods.

Keywords

• bis-acylated α-bis-hydroxymethyl-tetrahydrofuran
• oxidative cyclization
• ¹H-NMR
• ¹³C-NMR
• FTIR
• HRESIMS