T. Maeda, Mitsuru Kimoto, S. Wakahara
Jun 1, 1969
Citations
0
Influential Citations
5
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
The acid-catalyzed benzylidenation of L-sorbose (I) was studied. The reaction by Reichstein’s procedure gave a mixture of two diastereomeric 2,3:4,6-di-O-benzylidene-α-L-sorbofuranoses (III and IV), which were then successfully separated by preparative thin-layer chromatography. The use of slightly acidic conditions yielded l,3:4,6-di-O-benzylidene-β-L-sorbofuranose (XI), l,2:4,6-di-O-benzylidene-α- (XVII and XVIII) and-β-L-sorbofuranoses (XIX and XX), 1,2-O-benzylidene-α-L-sorbopyranoses (XXI and XXII), and 1,3-O-benzylidene-L-sorbose (XXIII). The absolute configurations at the acetal center of the five-membered benzylidene rings were assigned. A reaction sequence (I→(XXI, XXII\ightleftarrowsXXIII)→XI→IV→III) comparable with that of the ethylidenation of I was established.