Abstract
Herein we report that isobutyl-β-C-galactoside (IBCG) is also a promising inducer of gene expression in mammalian cells and report a new synthetic route to the compound that should make obtaining the multigram quantities of material required for animal studies more feasible. A convenient synthesis of IBCG, an inducer of genes controlled by the lac operon system in bacterial cells, was achieved in 5 steps from galactose in 81% overall yield without any chromatographic separation steps. An optimized microwave-assisted reaction at high concentration was key to making the C-glycosidic linkage. A Wittig reaction on a per-O-silylated rather than per-O-acetylated or -benzylated substrate proved most effective in installing the final carbon atom.
Original language | English |
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Pages (from-to) | 1539-1546 |
Number of pages | 8 |
Journal | Journal of Organic Chemistry |
Volume | 77 |
Issue number | 3 |
DOIs | |
State | Published - 3 Feb 2012 |
Externally published | Yes |