Holmstrøm Thomas, Raydan Daniel, Pedersen Christian Marcus
Department of Chemistry, Faculty of Science, University of Copenhagen, Universitetsparken 5, 2100 Copenhagen Ø, Denmark.
LAQV-REQUIMTE, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade NOVA de Lisboa, 2829-516 Caparica, Portugal.
Beilstein J Org Chem. 2020 Nov 17;16:2788-2794. doi: 10.3762/bjoc.16.229. eCollection 2020.
In this paper we describe the synthesis of a new carbohydrate-based building block functionalized with azido or amino groups on the 2 and 4 positions. The building block can be synthesized in anomerically pure form in only five scalable steps starting from commercially available levoglucosan. It was shown that the building block could undergo alkylations under strongly basic conditions. The building block with azido groups could furthermore take part in CuAAC reactions, generating derivatives with ester or carboxylic acid functionalities. In addition, the anomeric mixture of the building block was used for the synthesis of a molecule that could act as an emulsifier only in the presence of Zn ions.
在本文中，我们描述了一种新的基于碳水化合物的结构单元的合成方法，该结构单元在2位和4位上被叠氮基或氨基官能化。该结构单元可以从市售的左旋葡萄糖酐开始，仅通过五个可扩展步骤以异头物纯形式合成。结果表明，该结构单元在强碱性条件下可发生烷基化反应。带有叠氮基的结构单元还可以参与铜催化的叠氮化物-炔烃环加成反应（CuAAC反应），生成具有酯或羧酸官能团的衍生物。此外，该结构单元的异头物混合物用于合成一种仅在锌离子存在下才能充当乳化剂的分子。
