Chapter 15, Problem 65P

When compound C, which is often used to model a more frequently occurring unit in lignins, was ozonized, product D was obtained. In a variety of ways it has been established that the stereochemistry of the three-carbon side chain of such lignin units remains largely if not completely unchanged during oxidations like this.

For GC/MS, D was converted to its tetrakis(O-trimethylsilyl) derivative, which had $M{\cdot }^{+}$ 424 m/z. The IR spectrum of D had bands at 3000 $c{m}^{-1}$ (broad, strong) and 1710 $c{m}^{-1}$ (strong). Its ${}^{1}H$ NMR spectrum had peaks at $\delta$ 3.7 (multiplet, 3H) and $\delta$ 4.2 (doublet, 1H) after treatment with $D_{2}O$. Its $DEPT{}^{13}C$ NMR spectra had peaks at $\delta$ 64 $\left(C{H}_2\right)$, $\delta$ 75 (CH), $\delta 82$ (CH), and δd 177 (C). What is the structure of D, including its stereochemistry?