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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...
| Autores principales: | , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
Beilstein-Institut
2012
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| Materias: | |
| 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 |
| Sumario: | 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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