Reinvestigation of the mercuration-demercuration reaction on alkylated glycals: an improved method for the preparation of 2,3-dideoxy-alpha,beta-unsaturated carbohydrate enals |
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Authors: | Sagar Ram Pathak Rashmi Shaw Arun K |
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Institution: | Division of Medicinal and Process Chemistry, Central Drug Research Institute, Lucknow 226001, India. |
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Abstract: | Alkyl protected glycals can be easily converted into their corresponding alpha,beta-unsaturated enals (Perlin aldehydes) in good to very good yields by reaction with HgSO4 and aqueous 0.02 N H2SO4 in THF or 1,4-dioxane. While the formation of Perlin aldehydes from benzyl-protected glucal and arabinal was accomplished by refluxing the reaction mixture in 1,4-dioxane, the benzyl-protected galactal and methyl-protected glucal, galactal, and arabinal yielded aldehydes from this reaction at room temperature using THF or 1,4-dioxane as solvent. |
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Keywords: | Glycals HgSO4 Aqueous H2SO4 THF 1 4-Dioxane Perlin aldehyde |
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