Clarifying the Use of Benzylidene Protecting Group for D-(+)-Ribono-1,4-Lactone, an Essential Building Block in the Synthesis of <i>C</i>-Nucleosides

In the last two years, nucleosides analogues, a class of well-established bioactive compounds, have been the subject of renewed interest from the scientific community thanks to their antiviral activity. The COVID-19 global pandemic, indeed, spread light on the antiviral drug Remdesivir, an adenine &...

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Autores principales:	Silvana Casati, Paola Rota, Pietro Allevi, Alessandra Mingione, Roberta Ottria, Pierangela Ciuffreda
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	ribono-1,4-lactone 1-C-substituted nucleosides protecting groups cyclic acetals Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/410d6199b61543a1bed3d6d552438dd5
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spelling	oai:doaj.org-article:410d6199b61543a1bed3d6d552438dd52021-11-11T18:27:34ZClarifying the Use of Benzylidene Protecting Group for D-(+)-Ribono-1,4-Lactone, an Essential Building Block in the Synthesis of <i>C</i>-Nucleosides10.3390/molecules262164471420-3049https://doaj.org/article/410d6199b61543a1bed3d6d552438dd52021-10-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/21/6447https://doaj.org/toc/1420-3049In the last two years, nucleosides analogues, a class of well-established bioactive compounds, have been the subject of renewed interest from the scientific community thanks to their antiviral activity. The COVID-19 global pandemic, indeed, spread light on the antiviral drug Remdesivir, an adenine <i>C</i>-nucleoside analogue. This new attention of the medical community on Remdesivir prompts the medicinal chemists to investigate once again <i>C</i>-nucleosides. One of the essential building blocks to synthetize these compounds is the D-(+)-ribono-1,4-lactone, but some mechanistic aspects linked to the use of different carbohydrate protecting groups remain unclear. Here, we present our investigations on the use of benzylidene as a ribonolactone protecting group useful in the synthesis of <i>C</i>-purine nucleosides analogues. A detailed 1D and 2D NMR structural study of the obtained compounds under different reaction conditions is presented. In addition, a molecular modeling study at the B3LYP/6-31G* level of theory with the SM8 solvation model for CHCl<sub>3</sub> and DMSO to support the obtained results is used. This study allows for clarifying mechanistic aspects as the side reactions and structural rearrangements liked to the use of the benzylidene protecting group.Silvana CasatiPaola RotaPietro AlleviAlessandra MingioneRoberta OttriaPierangela CiuffredaMDPI AGarticleribono-1,4-lactone1-C-substituted nucleosidesprotecting groupscyclic acetalsOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6447, p 6447 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	ribono-1,4-lactone 1-C-substituted nucleosides protecting groups cyclic acetals Organic chemistry QD241-441
spellingShingle	ribono-1,4-lactone 1-C-substituted nucleosides protecting groups cyclic acetals Organic chemistry QD241-441 Silvana Casati Paola Rota Pietro Allevi Alessandra Mingione Roberta Ottria Pierangela Ciuffreda Clarifying the Use of Benzylidene Protecting Group for D-(+)-Ribono-1,4-Lactone, an Essential Building Block in the Synthesis of <i>C</i>-Nucleosides
description	In the last two years, nucleosides analogues, a class of well-established bioactive compounds, have been the subject of renewed interest from the scientific community thanks to their antiviral activity. The COVID-19 global pandemic, indeed, spread light on the antiviral drug Remdesivir, an adenine <i>C</i>-nucleoside analogue. This new attention of the medical community on Remdesivir prompts the medicinal chemists to investigate once again <i>C</i>-nucleosides. One of the essential building blocks to synthetize these compounds is the D-(+)-ribono-1,4-lactone, but some mechanistic aspects linked to the use of different carbohydrate protecting groups remain unclear. Here, we present our investigations on the use of benzylidene as a ribonolactone protecting group useful in the synthesis of <i>C</i>-purine nucleosides analogues. A detailed 1D and 2D NMR structural study of the obtained compounds under different reaction conditions is presented. In addition, a molecular modeling study at the B3LYP/6-31G* level of theory with the SM8 solvation model for CHCl<sub>3</sub> and DMSO to support the obtained results is used. This study allows for clarifying mechanistic aspects as the side reactions and structural rearrangements liked to the use of the benzylidene protecting group.
format	article
author	Silvana Casati Paola Rota Pietro Allevi Alessandra Mingione Roberta Ottria Pierangela Ciuffreda
author_facet	Silvana Casati Paola Rota Pietro Allevi Alessandra Mingione Roberta Ottria Pierangela Ciuffreda
author_sort	Silvana Casati
title	Clarifying the Use of Benzylidene Protecting Group for D-(+)-Ribono-1,4-Lactone, an Essential Building Block in the Synthesis of <i>C</i>-Nucleosides
title_short	Clarifying the Use of Benzylidene Protecting Group for D-(+)-Ribono-1,4-Lactone, an Essential Building Block in the Synthesis of <i>C</i>-Nucleosides
title_full	Clarifying the Use of Benzylidene Protecting Group for D-(+)-Ribono-1,4-Lactone, an Essential Building Block in the Synthesis of <i>C</i>-Nucleosides
title_fullStr	Clarifying the Use of Benzylidene Protecting Group for D-(+)-Ribono-1,4-Lactone, an Essential Building Block in the Synthesis of <i>C</i>-Nucleosides
title_full_unstemmed	Clarifying the Use of Benzylidene Protecting Group for D-(+)-Ribono-1,4-Lactone, an Essential Building Block in the Synthesis of <i>C</i>-Nucleosides
title_sort	clarifying the use of benzylidene protecting group for d-(+)-ribono-1,4-lactone, an essential building block in the synthesis of <i>c</i>-nucleosides
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/410d6199b61543a1bed3d6d552438dd5
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Clarifying the Use of Benzylidene Protecting Group for D-(+)-Ribono-1,4-Lactone, an Essential Building Block in the Synthesis of <i>C</i>-Nucleosides

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