期刊
TETRAHEDRON-ASYMMETRY
卷 26, 期 12-13, 页码 657-661出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2015.05.008
关键词
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资金
- National Research Foundation of Korea (NRF) - Ministry of Education, Science and Technology [2010-0022900, 2011-0029199]
- Yonsung Fine Chemicals Corporation
- Global Ph.D. Fellowship Grant
- National Research Foundation of Korea [2011-0029199, 2010-0022900] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
Concise and stereocontrolled syntheses of (+)-1-deoxynojirimycin and (2R,5R)-dihydroxymethyl-(3R,4R)dihydroxypyrrolidine [(+)-DMDP] were achieved via a diastereomerically enriched oxazine intermediate. The key strategies include the use of 1,3-oxazine as a chiral building block and diastereoselective nucleophilic addition to an aldehyde. Starting from readily available (R)-methyl 2-benzamido-3-((tertbutyldimethylsilyl)oxy)propanoate, (+)-1-deoxynojirimycin was synthesized in 11 steps and 26.2% overall yield while (+)-DMDP was synthesized in 11 steps and 27.1% overall yield, respectively. (C) 2015 Elsevier Ltd. All rights reserved.
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