Helvetica Chimica Acta p. 775 - 786 (1981)
Update date:2022-08-29
Topics:
Wyss, Heinz
Voegeli, Ulrich
Scheffold, Rolf
The 3-methoxymethyl derivatives of 2-methyl-D,L-threofuranose (10a) and 2-deoxy-2-methyl-D,L-erythrofuranose (11a) are prepared starting from 2-methyltetronic acid (1).The key step is the stereoselective reduction of the 3-oxo-function of 2-chloro-2-methyl-3-oxo-γ-butyrolacton (2) by sodiumborohydride, which proceeds predominantly anti with respect to the C, Cl-bond.The configuration of the reduction products has been established by 1H- and 13C-NMR.-spectroscopy.
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