Stereoselective Synthesis of 1- C -Diethylphosphonomethyl and -difluoromethyl Iminosugars from Sugar Lactams - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2022

Stereoselective Synthesis of 1- C -Diethylphosphonomethyl and -difluoromethyl Iminosugars from Sugar Lactams

Résumé

A strategy allowing the straightforward synthesis of 1-C-phosphonomethyl and 1-C-phosphonodifluoromethyl iminosugars is reported. Conversion of sugar lactams to the corresponding imines with Schwartz′s reagent followed by their reaction with LiCH2P(O)(OEt)2 and LiCF2P(O)(OEt)2 stereoselectively afforded the 1,2-cis and 1,2-trans glycosyl phosphonates, resp., in modest to good yields. Application of this methodol. to C-2 orthogonally protected sugar lactams paved the way to 2-acetamido- and 2-deoxy-1-C-phosphonomethyl iminosugars.

Domaines

Chimie organique
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Dates et versions

hal-03953681 , version 1 (11-04-2024)

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Citer

Thanh Van Tran, Jérôme Désiré, Nicolas Auberger, Yves Blériot. Stereoselective Synthesis of 1- C -Diethylphosphonomethyl and -difluoromethyl Iminosugars from Sugar Lactams. Journal of Organic Chemistry, 2022, 87 (11), pp.7581-7585. ⟨10.1021/acs.joc.2c00835⟩. ⟨hal-03953681⟩
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