Concise synthesis of C-1-cyano-iminosugars via a new Staudinger/aza Wittig/Strecker multicomponent reaction strategy

A new Staudinger/aza Wittig/Strecker multicomponent reaction sequence to C-1-cyano iminoalditols has been developed. When applied to 5-azidodeoxy-d-xylose and -d-glucose as substrates the method leads smoothly in good yield and with excellent stereoselectivity to respectively, 1,5-dideoxy-1,5-imino-d-idurono nitrile and 2,6-didesoxy-2,6-imino-d-glycero-d-ido-heptononitrile.

Graphical abstractThe Staudinger/aza Wittig/Strecker (SAWS) multicomponent reaction (MCR) sequence applied to azidodeoxy carbohydrate substrates leads smoothly in good yield and with excellent stereoselectivity to versatile C-glycosyl iminoalditol analogues which prove useful as building blocks en route to functionalized C-glycosyl iminoalditols able to inhibit human lysosomal β-glucocerebrosidase.Figure optionsDownload full-size imageDownload as PowerPoint slide