標題: General Homologation Strategy for Synthesis of L-glycero- and D-glycero-Heptopyranoses
作者: Mulani, Shaheen K.
Cheng, Kuang-Chun
Mong, Kwok-Kong T.
應用化學系
Department of Applied Chemistry
公開日期: 20-十一月-2015
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.
URI: http://dx.doi.org/10.1021/acs.orglett.5b02620
http://hdl.handle.net/11536/129374
ISSN: 1523-7060
DOI: 10.1021/acs.orglett.5b02620
期刊: ORGANIC LETTERS
Volume: 17
Issue: 22
起始頁: 5536
結束頁: 5539
顯示於類別:期刊論文