Stratingh Institute for Chemistry, University of Groningen, Groningen 9747 AG, The Netherlands.
Department of Biochemistry, Groningen Biochemistry & Biotechnology Institute, University of Groningen, Groningen 9747 AB, The Netherlands.
Org Lett. 2020 Jul 17;22(14):5622-5626. doi: 10.1021/acs.orglett.0c01986. Epub 2020 Jul 7.
Unprotected 3-keto-saccharides have become readily accessible via site-selective oxidation, but their protection-free functionalization is relatively unexplored. Here we show that protecting groups are obsolete in a variety of stereoselective modifications of our model substrate methyl α-glucopyranoside. This allows the preparation of rare sugars and the installation of click handles and reactive groups. To showcase the applicability of the methodology, maltoheptaose has been converted into a chemical probe, and the rare sugar evalose has been synthesized.
未受保护的 3-酮糖可通过选择性氧化轻易获得，但它们的无保护基官能化仍相对未知。在此，我们展示了在对模型底物甲基 α-吡喃葡萄糖苷进行多种立体选择性修饰时，保护基是多余的。这使得制备稀有糖以及安装点击试剂和反应基团成为可能。为了展示该方法的适用性，我们将麦芽七糖转化为化学探针，并合成了稀有糖艾杜糖。
