Journal
ORGANIC LETTERS
Volume 22, Issue 8, Pages 2981-2986Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c00732
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Funding
- National Key Technology R&D Program New Drug Innovation of China [2019ZX09301-106]
- NSFC [21232002, 21772007, 81930097]
- State Key Laboratory of Natural and Biomimetic Drugs
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A phenylselenoglycosylation reaction of glycal derivatives mediated by diphenyl diselenide and phenyliodine(III) bis(trifluoroacetate) under mild conditions is described. Stereoselective glycosylation has been achieved by installing fused carbonate on those glycals. 3,4-O-Carbonate galactals and 2,3-O-carbonate 2-hydroxyglucals are converted into corresponding glycosides in good yields with excellent beta-selectivity, resulting in 2-phenylseleno-2-deoxy-beta-galactosides and 2-phenylseleno-beta-mannosides which are good precursors of 2-deoxy-beta-galactosides and mannosides, respectively.
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