P(III) vs P(V): A P(V) Reagent for Thiophosphoramidate Linkages and Application to an Asymmetric Synthesis of a Cyclic Dinucleotide STING Agonist

Autor:	Hua Chia Tai, Ye Zhu, Sloan Ayers, Guanghui Zhu, Martin D. Eastgate, Bin Zheng, Ben Cohen, Miao Yu, Geoffrey E. Purdum, Chao Hang, Hyunsoo Park, Michael A. Schmidt, Adam Joseph Freitag, James Paulson, Siwei Guo, Changxia Yuan, Melda Sezen-Edmonds, Weiqing Fu, Rogers Amanda J, Jonathan G. Shackman, Jason Zhu, Ben Hritzko, Brian Lingfeng He, Daniel S. Treitler, Qinggang Wang
Rok vydání:	2021
Předmět:	Agonist Sting medicine.drug_class Stereochemistry Chemistry Reagent Yield (chemistry) Organic Chemistry medicine Enantioselective synthesis Membrane Proteins Indicators and Reagents Stereoselectivity
Zdroj:	The Journal of Organic Chemistry. 87:1934-1940
ISSN:	1520-6904 0022-3263
Popis:	A highly stereoselective synthesis of a cyclic dinucleotide (CDN) STING agonist containing two chiral thiophosphoramidate linkages is described. These rare, yet key functional groups were, for the first time, installed efficiently and with high diastereoselectivity using a specially designed P(V) reagent. By utilizing this strategy, the CDN was prepared in greater than sixteen-fold higher yield than the prior P(III) approach, with fewer hazardous reagents and chromatographic purifications.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::86f136684d522755cd8834b7b630c19b https://doi.org/10.1021/acs.joc.1c01055 Zobrazit plný text záznamu