期刊
ORGANIC LETTERS
卷 17, 期 6, 页码 1421-1424出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b00295
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- University Konstanz
Michael-type addition of thiolates to 2-nitro-D-glucal or to 2-nitro-D-galactal derivatives readily provides 2-deoxy-2-nitro-1-thioglycosides. Kinetic and thermodynamic reaction control permitted formation of either the alpha- or preferentially the beta-anomers, respectively. Addition of achiral and chiral thiourea derivatives to the reaction mixture increased the reaction rate; the outcome is substrate-controlled. The 2-deoxy-2-nitro-1-thioglycosides are excellent glycosyl donors under arylsulfenyl chloride/silver triflate (ArSCl/AgOTf) activation, and they provide, anchimerically assisted by the nitro group, mostly beta-glycosides.
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