S-Fluorenylmethyl protection of the cysteine side chain upon N(α)-Fmoc deprotection

Deprotection of an N(α)-Fmoc-protected glycocysteine derivative 7 with an excess of morpholine unexpectedly led to the fluorenylmethyl-protected thioether 8 in high yield. The suggested mechanism for this reaction comprises the addition of the cysteine thiolate on the exocyclic double bond of dibenz...

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Autores principales: Wehner, Johannes W, Lindhorst, Thisbe K
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3555517/
https://www.ncbi.nlm.nih.gov/pubmed/23365626
http://dx.doi.org/10.3762/bjoc.8.242
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author Wehner, Johannes W
Lindhorst, Thisbe K
author_facet Wehner, Johannes W
Lindhorst, Thisbe K
author_sort Wehner, Johannes W
collection PubMed
description Deprotection of an N(α)-Fmoc-protected glycocysteine derivative 7 with an excess of morpholine unexpectedly led to the fluorenylmethyl-protected thioether 8 in high yield. The suggested mechanism for this reaction comprises the addition of the cysteine thiolate on the exocyclic double bond of dibenzofulvene, which is formed during Fmoc deprotection. The influence of base concentration on this transprotection reaction was studied.
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spelling pubmed-35555172013-01-30 S-Fluorenylmethyl protection of the cysteine side chain upon N(α)-Fmoc deprotection Wehner, Johannes W Lindhorst, Thisbe K Beilstein J Org Chem Letter Deprotection of an N(α)-Fmoc-protected glycocysteine derivative 7 with an excess of morpholine unexpectedly led to the fluorenylmethyl-protected thioether 8 in high yield. The suggested mechanism for this reaction comprises the addition of the cysteine thiolate on the exocyclic double bond of dibenzofulvene, which is formed during Fmoc deprotection. The influence of base concentration on this transprotection reaction was studied. Beilstein-Institut 2012-12-10 /pmc/articles/PMC3555517/ /pubmed/23365626 http://dx.doi.org/10.3762/bjoc.8.242 Text en Copyright © 2012, Wehner and Lindhorst https://creativecommons.org/licenses/by/2.0https://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/2.0), 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 Letter
Wehner, Johannes W
Lindhorst, Thisbe K
S-Fluorenylmethyl protection of the cysteine side chain upon N(α)-Fmoc deprotection
title S-Fluorenylmethyl protection of the cysteine side chain upon N(α)-Fmoc deprotection
title_full S-Fluorenylmethyl protection of the cysteine side chain upon N(α)-Fmoc deprotection
title_fullStr S-Fluorenylmethyl protection of the cysteine side chain upon N(α)-Fmoc deprotection
title_full_unstemmed S-Fluorenylmethyl protection of the cysteine side chain upon N(α)-Fmoc deprotection
title_short S-Fluorenylmethyl protection of the cysteine side chain upon N(α)-Fmoc deprotection
title_sort s-fluorenylmethyl protection of the cysteine side chain upon n(α)-fmoc deprotection
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3555517/
https://www.ncbi.nlm.nih.gov/pubmed/23365626
http://dx.doi.org/10.3762/bjoc.8.242
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