N,N-Diacetylsialyl chloride--a novel readily accessible sialyl donor in reactions with neutral and charged nucleophiles in the absence of a promoter.

作者: Anna V. Orlova , Anna M. Shpirt , Nadezhda Y. Kulikova , Leonid O. Kononov

DOI: 10.1016/J.CARRES.2010.01.005

关键词: Organic chemistryChemistryGlycosylNucleophileAzideMedicinal chemistryGlycosyl donorChemical glycosylationSialic acidStereoselectivityPhosphate

摘要: Abstract N , -Diacetylneuraminic acid glycosyl chloride was prepared for the first time and made to react with various nucleophiles give corresponding α-glycosyl phosphate, β-glycosyl dibenzyl azide, α-phenyl thioglycoside xanthate in 65–82% yields high stereoselectivity while its reactions simple alcohols were not stereoselective. The new sialyl donor possible stereoselective synthesis of sialic phosphate α-configuration highly efficient β-configured phosphate.

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