Department of Pharmaceutical and Biomedical Sciences, University of Georgia, 250 West Green Street, Athens, Georgia 30602, United States.
Department of Biochemistry and Molecular Biology, University of Georgia, 120 East Green Street, Athens, Georgia 30602, United States.
J Org Chem. 2024 Mar 15;89(6):4225-4231. doi: 10.1021/acs.joc.3c02922. Epub 2024 Mar 1.
We describe the gram-scale synthesis of (-)-(1,2,3,4,5,6)-1,3-di(diamino)-1,3-diazido-2,5,6-tri--benzylstreptamine from streptomycin by (i) hydrolysis of the two streptomycin guanidine residues, (ii) reprotection of the amines as azides, (iii) protection of all alcohols as benzyl ethers, and (iv) glycosidic bond cleavage with HCl in methanol. Protocols for regioselective monodebenzylation and regioselective reduction of a single azide in the product are also described, providing four optically pure building blocks for exploitation in novel aminoglycoside synthesis.
我们描述了从链霉素通过以下步骤进行 (-)-(1,2,3,4,5,6)-1,3-二(二氨基)-1,3-二叠氮基-2,5,6-三--苄基链霉胺的克级合成：（i）胍基的水解，（ii）胺作为叠氮化物的重新保护，（iii）所有醇作为苄基醚的保护，以及（iv）在甲醇中用 HCl 进行糖苷键裂解。还描述了产物中单苄基化和单个叠氮化物的区域选择性还原的方案，提供了四个光学纯的构建块，用于新型氨基糖苷合成的开发。
