期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 81, 期 21, 页码 10569-10575出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b01575
关键词
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资金
- FAPESP (Research Supporting Foundation of the State of Sao Paulo) [2013/25504-1, 2013/18009-4, 2013/26399-7]
- CNPq
- CAPES [301079/2012-9, 140584/2015-3, 142396/2015-0, PROEX-1480644]
Highly stereoselective six-step syntheses of (-)-1-deoxyaltronojirimycin (altro-DNJ) and (+)-1-deoxymannojirimycin (manno-DNJ) from N-Cbz-O-TBDPS-L-serinal are described. Key transformations involve a two-step preparation of a functionalized dihydropyridin-3-one as a common intermediate followed by Luche reduction and dihydroxylation (for altro-DNJ). The same sequence employing an epoxidation/epoxide opening in place of dihydroxylation furnishes manno-DNJ.
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