Reinvestigation of the mercuration-demercuration reaction on alkylated glycals: an improved method for the preparation of 2,3-dideoxy-alpha,beta-unsaturated carbohydrate enals.
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.
Sagar
Ram
R
Division of Medicinal and Process Chemistry, Central Drug Research Institute, Lucknow 226001, India.
Pathak
Rashmi
R
Shaw
Arun K
AK
D000447:Aldehydes / Q000138:chemical synthesis*; D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D008628:Mercury / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism
D000447:Aldehydes; D002241:Carbohydrates; D008628:Mercury