• Journal of the Korean Wood Science and Technology
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• v.41 no.2
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• pp.149-157
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• 2013

The octopus type oligo-hydroxypropylene glycol ${\beta}$-D-glucopyranosides were successfully synthesized in this studies: the sterospecific compound of allyl 2, 3, 4, 6-tetra-O-acetyl-${\beta}$-D-glucopyranosides (1) was deacetylated with NaOMe in MeOH lead to allyl-${\beta}$-D-glucopyranoside (2) which was perallylated and followed by hydroboration and subsequent oxidation afforded (3-hydroxy-propyl) 2, 3, 4, 6-tetraO(3-hydroxy-propyl)-${\beta}$-D-glucopyranoside (4). As a result, not only allylpropylene glycol ${\beta}$-D-glucopyranosides (5, 7, and 9) but also hydroxypropylene glycol ${\beta}$-D-glucopyranosides (6, 8, and 10) were synthesized by repeated sequential perallylation followed by hydroboration/oxidation.