[KSCI] Korea Science Citation Index Service

http://dx.doi.org/10.5658/WOOD.2013.41.2.149

Synthesis of Octopus Type Trimethylene Glycol β-D-glucopyranosides

Kim, Yong Sik (Div. of Wood Chemistry & Microbiology, Dept. of Forest Products, Korea Forest Research Institute)
Kadla, John F. (Biomaterials Chemistry, Faculty of Forestry, University of British Columbia)

Publication Information

Journal of the Korean Wood Science and Technology / v.41, no.2, 2013 , pp. 149-157 More about this Journal

Abstract

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.

Keywords

hydroboration/oxidation; perallylation; oligo-hydroxypropylene glycol ${\beta}$ -D-glucopyranosides;

Citations & Related Records

Reference

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