Literature DB >> 34499517

Mild and Chemoselective Phosphorylation of Alcohols Using a Ψ-Reagent.

Michał Ociepa1, Kyle W Knouse1, David He1, Julien C Vantourout1, Dillon T Flood1, Natalia M Padial1, Jason S Chen2, Brittany B Sanchez2, Emily J Sturgell2, Bin Zheng3, Shenjie Qiu3, Michael A Schmidt3, Martin D Eastgate3, Phil S Baran1.   

Abstract

An operationally simple, scalable, and chemoselective method for the direct phosphorylation of alcohols using a P(V)-approach based on the Ψ-reagent platform is disclosed. The method features a broad substrate scope of utility in both simple and complex settings and provides access to valuable phosphorylated alcohols that would be otherwise difficult to obtain.

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Year:  2021        PMID： 34499517      PMCID： PMC8733960          DOI： 10.1021/acs.orglett.1c02736

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  25 in total

Review 1.  Biological phosphoryl-transfer reactions: understanding mechanism and catalysis.

Authors:  Jonathan K Lassila; Jesse G Zalatan; Daniel Herschlag
Journal:  Annu Rev Biochem       Date:  2011       Impact factor: 23.643

2.  The apparent acid ionization constants of some O-phosphorylated peptides and related compounds.

Authors:  G FOLSCH; R OSTERBERG
Journal:  J Biol Chem       Date:  1959-09       Impact factor: 5.157

3.  The oxorhenium(VII)-catalyzed direct condensation of phosphoric acid with an alcohol.

Authors:  Akira Sakakura; Mikimoto Katsukawa; Kazuaki Ishihara
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  Asymmetric phosphorylation through catalytic P(III) phosphoramidite transfer: enantioselective synthesis of D-myo-inositol-6-phosphate.

Authors:  Peter A Jordan; Katherine J Kayser-Bricker; Scott J Miller
Journal:  Proc Natl Acad Sci U S A       Date:  2010-05-03       Impact factor: 11.205

Review 5.  Synthesis of nucleoside phosphate and phosphonate prodrugs.

Authors:  Ugo Pradere; Ethel C Garnier-Amblard; Steven J Coats; Franck Amblard; Raymond F Schinazi
Journal:  Chem Rev       Date:  2014-08-21       Impact factor: 60.622

6.  Agarose derivatives of uridine diphosphate and N-acetylglucosamine for the purification of a galactosyltransferase.

Authors:  R Barker; K W Olsen; J H Shaper; R L Hill
Journal:  J Biol Chem       Date:  1972-11-25       Impact factor: 5.157

7.  Selective synthesis of phosphate monoesters by dehydrative condensation of phosphoric acid and alcohols promoted by nucleophilic bases.

Authors:  Akira Sakakura; Mikimoto Katsukawa; Kazuaki Ishihara
Journal:  Org Lett       Date:  2005-05-12       Impact factor: 6.005

8.  Unlocking P(V): Reagents for chiral phosphorothioate synthesis.

Authors:  Kyle W Knouse; Justine N deGruyter; Michael A Schmidt; Bin Zheng; Julien C Vantourout; Cian Kingston; Stephen E Mercer; Ivar M Mcdonald; Richard E Olson; Ye Zhu; Chao Hang; Jason Zhu; Changxia Yuan; Qinggang Wang; Peter Park; Martin D Eastgate; Phil S Baran
Journal:  Science       Date:  2018-08-02       Impact factor: 47.728

9.  Phosphate derivatives of AZT display enhanced selectivity of action against HIV 1 by comparison to the parent nucleoside.

Authors:  C McGuigan; C Nickson; J Petrik; A Karpas
Journal:  FEBS Lett       Date:  1992-09-28       Impact factor: 4.124

10.  A Phosphoramidite Analogue of Cyclotriphosphate Enables Iterative Polyphosphorylations.

Authors:  Jyoti Singh; Nicole Steck; Debaditya De; Alexandre Hofer; Alexander Ripp; Ilya Captain; Manfred Keller; Paul A Wender; Rashna Bhandari; Henning J Jessen
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-14       Impact factor: 15.336
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  1 in total

1.  Straightforward Synthesis of the Poly(ADP-ribose) Branched Core Structure.

Authors:  Rui Hagino; Keita Mozaki; Naoko Komura; Akihiro Imamura; Hideharu Ishida; Hiromune Ando; Hide-Nori Tanaka
Journal:  ACS Omega       Date:  2022-09-05
  1 in total

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