Hirao Cross-Coupling Reaction as an Efficient Tool to Build Non-natural C2-Phosphonylated Sugars

Olivier Monasson; Maciej Malinowski; Nadège Lubin-Germain; Angélique Ferry

doi:10.1055/a-1709-3305

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(15): 3414-3420
DOI: 10.1055/a-1709-3305

special topic

Bürgenstock Special Section 2021 – Future Stars in Organic Chemistry

Hirao Cross-Coupling Reaction as an Efficient Tool to Build Non-natural C2-Phosphonylated Sugars

Olivier Monasson‡

^aCY Cergy-Paris Université, BioCIS, CNRS, 5 mail Gay-Lussac, 95000 Cergy-Pontoise cedex, France

^bUniversité Paris-Saclay, BioCIS, CNRS, 5, rue J-B Clément, 92296 Châtenay-Malabry cedex, France

,

Maciej Malinowski ‡

^aCY Cergy-Paris Université, BioCIS, CNRS, 5 mail Gay-Lussac, 95000 Cergy-Pontoise cedex, France

^cFaculty of Chemistry, Warsaw University of Technology, ul. Noakowskiego 3, 00-664 Warsaw, Poland

,

Nadège Lubin-Germain

^aCY Cergy-Paris Université, BioCIS, CNRS, 5 mail Gay-Lussac, 95000 Cergy-Pontoise cedex, France

^bUniversité Paris-Saclay, BioCIS, CNRS, 5, rue J-B Clément, 92296 Châtenay-Malabry cedex, France

,

Angélique Ferry∗

^aCY Cergy-Paris Université, BioCIS, CNRS, 5 mail Gay-Lussac, 95000 Cergy-Pontoise cedex, France

^bUniversité Paris-Saclay, BioCIS, CNRS, 5, rue J-B Clément, 92296 Châtenay-Malabry cedex, France

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

A range of C2-phosphonylated sugars have been accessed through a palladium-catalyzed Hirao cross-coupling on 2-iodoglycals using trialkylphosphites as phosphorylating reagents. The developed conditions led to the creation of an unnatural C–P bond on sugars and proved to be compatible with diversely protected glycals (acetyl-, benzyl-, PMB-protected) as well as with unprotected substrates. Several monosaccharides and one disaccharide have been synthesized by applying this methodology. Deprotection conditions are also described.

Key words

phosphonylation - cross-coupling - 2-iodoglycals - palladium catalysis - glycoanalogues

Volltext

Referenzen

References

1a Wang Z, Cole PA. Methods Enzymol. 2014; 548: 1
1b Cheng H.-C, Qi RZ, Paudel H, Zhu H.-J. Enzyme Res. 2011; 794089
1c Saier MH. Jr. J. Mol. Microbiol. Biotechnol. 2001; 3: 325
1d Deutscher J, Aké FM. D, Derkaoui M, Zébré AC, Cao TN, Bouraoui H, Kentache T, Mokhtari A, Milohanic E, Joyet P. Microbiol. Mol. Biol. Rev. 2014; 78: 231

2a Ardito F, Giuliani M, Perrone D, Troiano G, Lo Muzio L. Int. J. Mol. Med. 2017; 40: 271
2b Pawson T, Scott JD. Trends Biochem. Sci. 2005; 30: 286

3a Deutscher J, Francke C, Postma PW. Microbiol. Mol. Biol. Rev. 2006; 70: 939
3b Roy S, Vivoli Vega M, Harmer NJ. Catalysts 2019; 9: 29
3c Somavanshi R, Ghosh B, Sourjik V. PLOS Biol. 2016; 14: e2000074

4a Hoffmeister D, Yang J, Liu L, Thorson JS. Proc. Natl. Acad. Sci. U.S.A. 2003; 100: 13184
4b Yang J, Fu X, Jia Q, Shen J, Biggins JB, Jiang J, Zhao J, Schmidt JJ, Wang PG, Thorson JS. Org. Lett. 2003; 5: 2223
4c Ritte G, Heydenreich M, Mahlow S, Haebel S, Kötting O, Steup M. FEBS Lett. 2006; 580: 4872

5a Nicotra F. Top. Curr. Chem. 1997; 187: 55
5b Yang Y, Yu B. Chem. Rev. 2017; 117: 12281
5c Lee DY. W, He M. Curr. Top. Med. Chem. 2005; 5: 1333

6 Dharuman S, Vankar YD. Org. Lett. 2014; 16: 1172

Selected articles:

7a Rodriguez MA, Boutureira O, Matheu MI, Diaz Y, Castillon S, Seeberger PH. J. Org. Chem. 2007; 72: 8998
7b Hussain N, Bhardwaj M, Ahmed A, Mukherjee D. Org. Lett. 2019; 21: 3034
7c Jana S, Rainier JD. Org. Lett. 2013; 15: 4426
7d Cobo I, Matheu MI, Castillon S, Boutureira O, Davis BG. Org. Lett. 2012; 14: 1728
7e Chemler SR, Iserloh U, Danishefsky SJ. Org. Lett. 2001; 3: 2949
7f Bordessa A, Ferry A, Lubin-Germain N. J. Org. Chem. 2016; 81: 12459
7g de Robichon M, Bordessa A, Lubin-Germain N, Ferry A. J. Org. Chem. 2019; 84: 3328
7h Esteves HA, Darbem MP, Pimenta DC, Stefani HA. Eur. J. Org. Chem. 2019; 7384
7i Mestre J, Lishchynskyi A, Castillon S, Boutureira O. J. Org. Chem. 2018; 83: 8150
7j Mestre J, Castillon S, Boutureira O. J. Org. Chem. 2019; 84: 15087
7k Soares-Paulino AA, Stefani HA. Eur. J. Org. Chem. 2020; 3847
7l Darbem MP, Esteves HA, de Oliveira IM, Pimenta DC, Stefani HA. ChemCatChem 2020; 12: 576
7m Malinowski M, Tran TV, de Robichon M, Lubin-Germain N, Ferry A. Adv. Synth. Catal. 2020; 362: 1184

8 Al-Shuaeeb RA. A, Montoir D, Alami M, Messaoudi S. J. Org. Chem. 2017; 82: 6720
9 Malinowski M, Banoun C, de Robichon M, Lubin-Germain N, Ferry A. Eur. J. Org. Chem. 2021; 1521
10 Hirao T, Masunaga T, Ohshiro Y, Agawa T. Synthesis 1981; 56
11 Demmer CS, Krogsgaard-Larsen N, Bunch L. Chem. Rev. 2011; 111: 7981
12 Di Bussolo V, Caselli M, Pineschi M, Crotti P. Org. Lett. 2003; 5: 2173

Zusatzmaterial

Supporting Information