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Synlett 1991; 1991(3): 171-172
DOI: 10.1055/s-1991-20666
DOI: 10.1055/s-1991-20666
letter
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Ring Opening of C-Glycosides under Mild Conditions
Further Information
Publication History
Publication Date:
07 March 2002 (online)
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C-glycosides 2, 4, 7 and 12 react with dimethylboron bromide to form the acyclic alkenes 5, 6, 8 and 13 respectively. In this reaction, the ether linkage of the tetrahydropyran ring is opened without cleavage of the acetoxy groups. Alkene 13 (E,4R,5S,6R)-4,5,6,7-tetraacetoxy-2-heptenoic acid) is an important intermediate in the synthesis of KDO (3-deoxy-D-manno-2-octulosonic acid).