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:	Zheng B; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., Hang C; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., Zhu J; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., Purdum GE; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., Sezen-Edmonds M; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., Treitler DS; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., Yu M; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., Yuan C; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., Zhu Y; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., Freitag A; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., Guo S; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., Zhu G; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., Hritzko B; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., Paulson J; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., Shackman JG; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., He BL; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., Fu W; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., Tai HC; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., Ayers S; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., Park H; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., Eastgate MD; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., Cohen B; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., Rogers A; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., Wang Q; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., Schmidt MA; Bristol Myers Squibb, Chemical Process Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
Jazyk:	angličtina
Zdroj:	The Journal of organic chemistry [J Org Chem] 2022 Feb 18; Vol. 87 (4), pp. 1934-1940. Date of Electronic Publication: 2021 Jul 07.
DOI:	10.1021/acs.joc.1c01055
Abstrakt:	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 16-fold higher yield than the prior P(III) approach, with fewer hazardous reagents and chromatographic purifications.
Databáze:	MEDLINE
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