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

Thanh Van Tran, Jérôme Désiré, Nicolas Auberger, Yves Blériot

The Journal of organic chemistry 2022 Jun 03

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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, respectively, in modest to good yields. Application of this methodology to C-2 orthogonally protected sugar lactams paved the way to 2-acetamido- and 2-deoxy-1-C-phosphonomethyl iminosugars.

Citation

Thanh Van Tran, Jérôme Désiré, Nicolas Auberger, Yves Blériot. Stereoselective Synthesis of 1-C-Diethylphosphonomethyl and -difluoromethyl Iminosugars from Sugar Lactams. The Journal of organic chemistry. 2022 Jun 03;87(11):7581-7585