138736-93-3Relevant articles and documents
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.
A novel approach toward the synthesis of chiral 2,3-dideoxy nucleosides and their carbocyclic analogues
Lee-Ruff,Wan,Jiang
, p. 2114 - 2118 (2007/10/02)
Photochemical ring-expansion of chiral 2(S),3(R)-bis [(benzoyloxy)methyl]cyclobutanone (3) in the presence of alcohols and acidic N-H functional groups gives anomeric mixtures of acetals and N-amino acetals, respectively, with retention of stereochemistry