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Issue 40, 2012
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Synthesis of β-C-galactosyl D- and L-alanines

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Synthesis of β-C-D-galactosyl D- and L-alanines is carried out via a highly stereoselective Grignard reaction of glycosyl iodides, Sharpless dihydroxylation and SN2 displacement of the corresponding mesylate or tosylate. Alternatively, attempted triflation of the intermediate alcohols triggers a stereoselective debenzylative cyclization leading to interesting bicyclic trans-fused compounds.

Graphical abstract: Synthesis of β-C-galactosyl d- and l-alanines

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The article was received on 04 Jun 2012, accepted on 16 Aug 2012 and first published on 21 Aug 2012

Article type: Paper
DOI: 10.1039/C2OB26078F
Citation: Org. Biomol. Chem., 2012,10, 8132-8139
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    Synthesis of β-C-galactosyl D- and L-alanines

    V. N. Thota, J. Gervay-Hague and S. S. Kulkarni, Org. Biomol. Chem., 2012, 10, 8132
    DOI: 10.1039/C2OB26078F

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