Liu Yichu, Xu Xiaoyan, Gao Qi, Yan Shiqiang, Li Yingxia, Ding Ning
Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 201203, China.
China State Institute of Pharmaceutical Industry, Shanghai 201203, China.
Bioorg Med Chem Lett. 2017 Apr 15;27(8):1795-1798. doi: 10.1016/j.bmcl.2017.02.055. Epub 2017 Feb 24.
A versatile strategy for the synthesis of 6″-functionalized α-GalCers by using NAP ether group for permanent hydroxyl protection was developed, which provide the flexibility necessary for the incorporation of a wide range of functional groups in target molecules including alkyne, azide, thiol that are intolerant to Pd-catalyzed hydrogenolysis as well as other functionalities like carboxylic acid and amine. This strategy is also adaptable to other glycoconjugate synthesis especially those containing clickable tags and unsaturated functionalities.
开发了一种通用策略，通过使用NAP醚基团进行永久性羟基保护来合成6″-官能化α-半乳糖神经酰胺，该策略为在目标分子中引入广泛的官能团提供了必要的灵活性，这些官能团包括对钯催化氢解不耐受的炔烃、叠氮化物、硫醇以及其他官能团，如羧酸和胺。该策略也适用于其他糖缀合物的合成，特别是那些含有可点击标签和不饱和官能团的糖缀合物。
