A Convenient Protecting Group for Uridine Ureido Nitrogen: (4,4′-Bisfluorophenyl)methoxymethyl Group

Abstract

(4,4′-Bisfluorophenyl)methoxymethyl (BFPM) group of uridine ureido nitrogen shows good relative stability in a variety of chemical transformation reactions for uridine. The BFPM group can be cleaved by 2% of TFA in CH₂Cl₂ without affecting the Boc group.

Key words

uridine - ureido nitrogen - diarylmethoxymethyl group - [bis(4-fluorophenyl)methoxy]methyl group - chemical transformations - muraymycin synthesis

• References

• 1a Arbour CA, Imperiali B. Bioorg. Med. Chem. 2020; 28: 115661
• 1b Patel B, Kerr RV, Malde AK, Zunk M, Bugg TD, Grant G, Rudrawar S. ChemMedChem 2020; 15: 1429
• 1c Wiegmann D, Koppermann S, Ducho C. Molecules 2018; 23: 3085
• 1d Wiegmann D, Koppermann S, Wirth M, Niro G, Leyerer K, Ducho C. Beilstein J. Org. Chem. 2016; 12: 769
• 1e Shelton J, Lu X, Hollenbaugh JA, Cho JH, Amblard F, Schinazi RF. Chem. Rev. 2016; 116: 14379
• 1f Wiegmann D, Koppermann S, Wirth M, Niro G, Leyerer K, Ducho C. J. Org. Chem. 2016; 12: 769
• 1g Serpi M, Ferrari V, Pertusati F. J. Med. Chem. 2016; 59: 10343
• 1h Yamamoto T, Koyama H, Kurajoh M, Shoji T, Tsutsumi Z, Moriwaki Y. Clin. Chim. Acta 2011; 412: 1712
• 1i Winn M, Goss RJ. M, Kimura K, Bugg TD. H. Nat. Prod. Rep. 2010; 27: 279

Reports from our group:
• 2a Mitachi K, Kansal R, Hevener K, Gillman C, Yun H-G, Husain M, Miranda-Carboni G, Glazer E, Clemons WM, Kurosu M. J. Med. Chem. 2020; 63: 10855
• 2b Kurosu M. Future Med. Chem. 2019; 11: 927
• 2c Mitachi K, Kurosu SM, Gillman CD, Yun H-G, Clemons WM, Kurosu M. MethodsX 2019; 6: 2305
• 2d Mitachi K, Kurosu S, Eslamimehr S, Lemieux M, Ishizaki Y, Clemons W, Kurosu M. Org. Lett. 2019; 21: 876
• 2e Mitachi K, Yun H-G, Kurosu SM, Eslamimehr S, Lemieux MR, Klaić L, Clemons WM, Kurosu M. ACS Omega 2018; 3: 1726
• 2f Kurosu M. J. Mol. Pharm. Org. Process Res. 2018; 6: 141
• 2g Mitachi K, Aleiwi BA, Schneider CM, Siricilla S, Kurosu M. J. Am. Chem. Soc. 2016; 138: 12975
• 2h Siricilla S, Mitachi K, Wan B, Franzblau SG, Kurosu M. J. Antibiot. 2015; 68: 271
• 2i Wang Y, Siricilla S, Aleiwi BA, Kurosu M. Chem. Eur. J. 2013; 19: 13847
• 2j Kurosu M, Li K. Heterocycles 2009; 77: 217
• 2k Kurosu M, Li K, Crick DC. Org. Lett. 2009; 11: 2393

Reports from other groups:
• 2l Ref. 1b.
• 2m Ref. 1c.
• 2n Biecker AL, Liu X, Thorson JS, Yang Z, Van Lanen SG. Molecules 2019; 24: 433
• 2o Ichikawa S, Yamaguchi M, Matsuda A. Curr. Med. Chem. 2015; 22: 3951
• 2p Knapp S, Nandan SR. J. Org. Chem. 1994; 59: 281
• 2q Heib A, Niro G, Weck SC, Koppermann S, Ducho C. Molecules 2020; 25: 22
• 2r Leyerer K, Koppermann S, Ducho C. Eur. J. Org. Chem. 2019; 7420
• 2s Katsuyama A, Ichikawa S. Chem. Pharm. Bull. 2018; 66: 123
• 2t Yamashita A, Norton E, Peterson PJ, Rasmussen BA, Singh G, Yang Y, Mansour TS, Ho DM. Bioorg. Med. Chem. Lett. 2003; 13: 3345
• 3a Jarowickia K, Kocienski P. J. Chem. Soc., Perkin Trans. 1 1999; 1589
• 3b Kunz H, Waldman H. Protecting Groups . In Comprehensive Organic Synthesis, Vol. 6, Chap. 3.1. Trost BM, Fleming I. Pergamon Press; Oxford: 1991: 631
• 4a Aleiwi BA, Kurosu M. Tetrahedron Lett. 2012; 53: 3758
• 4b Connor DS, Klein GW, Taylor GN, Boeckman RK, Medwid JB. Org. Synth. 1972; 52: C10
• 4c Hanessian S, Kloss J, Sugawara T. J. Am. Chem. Soc. 1986; 108: 2758
• 4d Goff DA, Harris RN, Bottaro JC, Bedford CD. J. Org. Chem. 1986; 51: 4711
• 4e Prakash TP, Manoharan M, Kawasaki AM, Fraser AS, Lesnik EA, Sioufi N, Leeds JM, Teplova M, Egli M. Biochemistry 2002; 41: 11642
• 5a Wang Y, Kurosu M. Tetrahedron 2012; 68: 4797
• 5b Kurosu M, Li K. Synthesis 2009; 21: 3633
• 5c Kurosu M, Li K. Org. Lett. 2009; 11: 911
• 5d Kurosu M, Biswas K, Crick DC. Org. Lett. 2007; 9: 1141
• 6a Takahashi D, Yano T, Fukui T. Org. Lett. 2012; 14: 4514
• 6b Saudi M, van Aerschot A. Molecules 2013; 18: 8524
• 6c Mezaache R, Harkat H, Obszynski J, Benkouider A, Blanc A, Weibel JM, Pale P. Tetrahedron Lett. 2014; 55: 7167
• 6d Li J, Zhang X, Shen H, Liu Q, Pan J, Hu W, Chen C. Adv. Synth. Catal. 2015; 357: 3115
• 6e Howard KT, Duffy BC, Linaburg MR, Chisholm JD. Org. Biomol. Chem. 2016; 14: 1623
• 6f Tran VH, La MT, Kim HK. Org. Biomol. Chem. 2019; 17: 6221