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- W2034396599 abstract "Abstract Kinetically controlled O-isopropylidenation of common 2,6-anhydro-1-deoxy-1-nitroalditols (β- d -glycopyranosylnitromethanes) derived from d -glucose, d -galactose, and d -mannose with 2-methoxypropene in 1,2-dimethoxyethane catalyzed with 4-toluenesulfonic acid afforded high yields of 2,3;4,6-di-O-isopropylidene acetals. With d -mannose, the bisacetal was also obtained in quantitative yield by reaction with 2,2-dimethoxypropane. Mono-O-benzylidenation of the starting compounds with benzaldehyde dimethyl acetal followed by O-isopropylidenation led to 4,6-O-benzylidene-2,3-O-isopropylidene acetals having better solubilities in non-polar solvents than the di-O-isopropylidene acetals. Di-O-benzylidenation of β- d -mannopyranosylnitromethane gave both (endo-2,3):4,6- and (exo-2,3):4,6-di-O-benzylidene acetals. Transacetalation of 1-deoxy-1-nitro- d -mannitol with 2,2-dimethoxypropane followed by 2-O-acetylation and β-elimination of the acetoxy group afforded (E)-1,2-dideoxy-2,4:5,6-di-O-isopropylidene-1-nitro- d -arabino-hex-1 -enitol." @default.
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- W2034396599 title "Full acetals of β-d-glycopyranosylnitromethanes and a 1,2-dideoxy-1-nitroalk-1-enitol derived from common hexoses" @default.
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- W2034396599 doi "https://doi.org/10.1016/s0008-6215(97)00203-6" @default.
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