|標題:||General Homologation Strategy for Synthesis of L-glycero- and D-glycero-Heptopyranoses|
|作者:||Mulani, Shaheen K.|
Mong, Kwok-Kong T.
Department of Applied Chemistry
|摘要:||A general and stereospecific homologation strategy for the synthesis of heptopyranosides is reported. The strategy employs the Wittig olefination and proline-catalyzed a-aminoxylation to achieve one carbon elongation and stereoselective hydroxylation at the C6 position, respectively. The l-glycero- and d-glycero-heptopyranosides can be obtained with nearly perfect stereoselectivity. Further study reveals the difference in the chemical shift of the C6 proton of l/d-glycero-heptopyranosyl diastereomers, which is found to be useful for assignment of the configuration of heptopyranosides.|
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