Effect of uridine protecting groups on the diastereoselectivity of uridine-derived aldehyde 5’-alkynylation

The 5’-alkynylation of uridine-derived aldehydes is described. The addition of alkynyl Grignard reagents on the carbonyl group is significantly influenced by the 2’,3’-di-O-protecting groups (R(1)): O-alkyl groups led to modest diastereoselectivities (65:35) in favor of the 5’R-isomer, whereas O-sil...

Descripción completa

Detalles Bibliográficos
Autores principales: Ben Othman, Raja, Fer, Mickaël J, Le Corre, Laurent, Calvet-Vitale, Sandrine, Gravier-Pelletier, Christine
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5550804/
https://www.ncbi.nlm.nih.gov/pubmed/28845198
http://dx.doi.org/10.3762/bjoc.13.153
_version_ 1783256189065232384
author Ben Othman, Raja
Fer, Mickaël J
Le Corre, Laurent
Calvet-Vitale, Sandrine
Gravier-Pelletier, Christine
author_facet Ben Othman, Raja
Fer, Mickaël J
Le Corre, Laurent
Calvet-Vitale, Sandrine
Gravier-Pelletier, Christine
author_sort Ben Othman, Raja
collection PubMed
description The 5’-alkynylation of uridine-derived aldehydes is described. The addition of alkynyl Grignard reagents on the carbonyl group is significantly influenced by the 2’,3’-di-O-protecting groups (R(1)): O-alkyl groups led to modest diastereoselectivities (65:35) in favor of the 5’R-isomer, whereas O-silyl groups promoted higher diastereoselectivities (up to 99:1) in favor of the 5’S-isomer. A study related to this protecting group effect on the diastereoselectivity is reported.
format Online
Article
Text
id pubmed-5550804
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-55508042017-08-25 Effect of uridine protecting groups on the diastereoselectivity of uridine-derived aldehyde 5’-alkynylation Ben Othman, Raja Fer, Mickaël J Le Corre, Laurent Calvet-Vitale, Sandrine Gravier-Pelletier, Christine Beilstein J Org Chem Full Research Paper The 5’-alkynylation of uridine-derived aldehydes is described. The addition of alkynyl Grignard reagents on the carbonyl group is significantly influenced by the 2’,3’-di-O-protecting groups (R(1)): O-alkyl groups led to modest diastereoselectivities (65:35) in favor of the 5’R-isomer, whereas O-silyl groups promoted higher diastereoselectivities (up to 99:1) in favor of the 5’S-isomer. A study related to this protecting group effect on the diastereoselectivity is reported. Beilstein-Institut 2017-08-04 /pmc/articles/PMC5550804/ /pubmed/28845198 http://dx.doi.org/10.3762/bjoc.13.153 Text en Copyright © 2017, Ben Othman et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Ben Othman, Raja
Fer, Mickaël J
Le Corre, Laurent
Calvet-Vitale, Sandrine
Gravier-Pelletier, Christine
Effect of uridine protecting groups on the diastereoselectivity of uridine-derived aldehyde 5’-alkynylation
title Effect of uridine protecting groups on the diastereoselectivity of uridine-derived aldehyde 5’-alkynylation
title_full Effect of uridine protecting groups on the diastereoselectivity of uridine-derived aldehyde 5’-alkynylation
title_fullStr Effect of uridine protecting groups on the diastereoselectivity of uridine-derived aldehyde 5’-alkynylation
title_full_unstemmed Effect of uridine protecting groups on the diastereoselectivity of uridine-derived aldehyde 5’-alkynylation
title_short Effect of uridine protecting groups on the diastereoselectivity of uridine-derived aldehyde 5’-alkynylation
title_sort effect of uridine protecting groups on the diastereoselectivity of uridine-derived aldehyde 5’-alkynylation
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5550804/
https://www.ncbi.nlm.nih.gov/pubmed/28845198
http://dx.doi.org/10.3762/bjoc.13.153
work_keys_str_mv AT benothmanraja effectofuridineprotectinggroupsonthediastereoselectivityofuridinederivedaldehyde5alkynylation
AT fermickaelj effectofuridineprotectinggroupsonthediastereoselectivityofuridinederivedaldehyde5alkynylation
AT lecorrelaurent effectofuridineprotectinggroupsonthediastereoselectivityofuridinederivedaldehyde5alkynylation
AT calvetvitalesandrine effectofuridineprotectinggroupsonthediastereoselectivityofuridinederivedaldehyde5alkynylation
AT gravierpelletierchristine effectofuridineprotectinggroupsonthediastereoselectivityofuridinederivedaldehyde5alkynylation

Ejemplares similares