743477-83-0Relevant academic research and scientific papers
A Stereocontrolled Synthesis of a Phosphorothioate Cyclic Dinucleotide-Based STING Agonist
Kempson, James,Zhang, Huiping,Hou, Xiaoping,Cornelius, Lyndon,Zhao, Rulin,Wang, Bei,Hong, Zhenqiu,Oderinde, Martins S.,Pawluczyk, Joseph,Wu, Dauh-Rurng,Sun, Dawn,Li, Peng,Yip, Shiuhang,Smith, Aaron,Caceres-Cortes, Janet,Aulakh, Darpandeep,Sarjeant, Amy A.,Park, Peter K.,Harikrishnan, Lalgudi S.,Qin, Lan-Ying,Dodd, Dharmpal S.,Fink, Brian,Vite, Gregory,Mathur, Arvind
, p. 8851 - 8861 (2021/06/30)
We describe a stereodefined synthesis of the newly identified non-natural phosphorothioate cyclic dinucleotide (CDN) STING agonist, BMT-390025. The new route avoids the low-yielding racemic approach using P(III)-based reagents, and the stereospecific assembly of the phosphorothioate linkages are forged via the recently invented P(V)-based platform of the so-called PSI (Ψ) reagent system. This P(V) approach allows for the complete control of chirality of the P-based linkages and enabled conclusive evidence of the absolute configuration. The new approach offers robust procedures for preparing the stereodefined CDN in eight steps starting from advanced nucelosides, with late-stage direct drop isolations and telescoped steps enabling an efficient scale-up that proceeded in an overall 15% yield to produce multigram amounts of the CDN.
Synthesis of novel spiro[2.3]hexane carbocyclic nucleosides via enzymatic resolution
Bondada, Lavanya,Gumina, Giuseppe,Nair, Ranjeet,Xing, Hai Ning,Schinazi, Raymond F.,Chu, Chung K.
, p. 2531 - 2534 (2007/10/03)
(Matrix Presented) Novel R- and S-spiro[2.3]hexane nucleosides have been synthesized. The key step involved the Pseudomonas cepacia lipase catalyzed resolution of racemic compound 2, synthesized in seven steps starting from diethoxyketene and diethyl fuma
