Preparation of 1-C-glycosyl aldehydes by reductive hydrolysis |
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Authors: | Sipos Szabolcs Jablonkai István |
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Institution: | Institute of Biomolecular Chemistry, Chemical Research Center, Hungarian Academy of Sciences, PO Box 17, 1525 Budapest, Hungary |
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Abstract: | Reductive hydrolysis of various protected glycosyl cyanides was carried out using DIBAL-H to form aldimine alane intermediates which were then hydrolyzed under mildly acidic condition to provide the corresponding aldehyde derivatives. While 1-C-formyl glycal and 2-deoxy glycosyl derivatives were stable during isolation and storage 1-C-glycosyl formaldehydes in the gluco, galacto and manno series were sensitive and decomposition occurred by 2-alkyloxy elimination. A one-pot method using N,N′-diphenylethylenediamine to trap these aldehydes in stable form was developed. Reductive hydrolysis of glycosyl cyanides offers valuable aldehyde building blocks in a convenient way which can be applied in the synthesis of complex C-glycosides. |
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Keywords: | Glycosyl cyanides 1-C-Glycosyl aldehydes DIBAL-H β-Elimination 1 3-Imidazolidine derivative |
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