Large-scale synthesis of all stereoisomers of a 2,3-unsaturated C-glycoside scaffold.

All stereoisomers of a highly functionalized 2,3-unsaturated C-glycoside can be accessed in 10-100 g quantities from readily available starting materials and reagents in 3-7 steps. These chiral scaffolds contain three stereogenic centers along with orthogonally protected functional groups for downstream reactivity.

Citation

Baudouin Gerard, Jean-Charles Marié, Bhaumik A Pandya, Maurice D Lee, Haibo Liu, Lisa A Marcaurelle. Large-scale synthesis of all stereoisomers of a 2,3-unsaturated C-glycoside scaffold. The Journal of organic chemistry. 2011 Mar 18;76(6):1898-901

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PMID: 21341742

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