Université de Poitiers, IC2MP, UMR CNRS 7285, Equipe "OrgaSynth", Groupe Glycochimie 4 rue Michel Brunet, 86073 Poitiers cedex 9, France.
J Org Chem. 2022 Jun 3;87(11):7581-7585. doi: 10.1021/acs.joc.2c00835. Epub 2022 May 18.
A strategy allowing the straightforward synthesis of 1--phosphonomethyl and 1--phosphonodifluoromethyl iminosugars is reported. Conversion of sugar lactams to the corresponding imines with Schwartz's reagent followed by their reaction with LiCHP(O)(OEt) and LiCFP(O)(OEt) stereoselectively afforded the 1,2- and 1,2- 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--phosphonomethyl iminosugars.
报道了一种可直接合成 1--膦酸甲基和 1--膦二氟甲基亚氨基糖的策略。用施瓦茨试剂将糖内酰胺转化为相应的亚胺，然后与 LiCHP(O)(OEt)和 LiCFP(O)(OEt)反应，分别以中等至良好的收率立体选择性地得到 1,2-和 1,2-糖基膦酸酯。该方法在 C-2 位保护的糖内酰胺上的应用为 2-乙酰氨基-和 2-脱氧-1--膦酸甲基亚氨基糖的合成铺平了道路。
