Ring Opening ofC-Glycosides under Mild Conditions
- 1 January 1991
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1991 (03) , 171-172
- https://doi.org/10.1055/s-1991-20666
Abstract
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).Keywords
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