Abstract
The D-arabino, L-lyxo, and L-xylo
isomers of 3-hexulose have been synthesized by oxidation, with chromium
trioxide in acetic acid, of fully acetylated derivatives of
3,4-0-ethylidene-D-mannitol, 3,4-0-ethylidene-L-iditol, and 2,4-O-benzylidene-D-glucitol, respectively.
The D-ribo isomer has been obtained from the L-lyxo compound by inversion at C5. The
3-hexuloses were characterized as their crystalline di-O-isopropylidene derivatives: the
arabino-
and ribo-hexuloses
each give three diacetals. The stereochemistry of
these derivatives, and of the spiro-acetals of
ketoses in general, is discussed.
Cited by
31 articles.
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