Solution-phase automated synthesis of an α-amino aldehyde as a versatile intermediate

A solution-phase automated synthesis of the versatile synthetic intermediate, Garner’s aldehyde, was demonstrated. tert-Butoxycarbonyl (Boc) protection, acetal formation, and reduction of the ester to the corresponding aldehyde were performed utilizing our originally developed automated synthesizer,...

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Detalles Bibliográficos
Autores principales: Masui, Hisashi, Yosugi, Sae, Fuse, Shinichiro, Takahashi, Takashi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5301908/
https://www.ncbi.nlm.nih.gov/pubmed/28228851
http://dx.doi.org/10.3762/bjoc.13.13
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author Masui, Hisashi
Yosugi, Sae
Fuse, Shinichiro
Takahashi, Takashi
author_facet Masui, Hisashi
Yosugi, Sae
Fuse, Shinichiro
Takahashi, Takashi
author_sort Masui, Hisashi
collection PubMed
description A solution-phase automated synthesis of the versatile synthetic intermediate, Garner’s aldehyde, was demonstrated. tert-Butoxycarbonyl (Boc) protection, acetal formation, and reduction of the ester to the corresponding aldehyde were performed utilizing our originally developed automated synthesizer, ChemKonzert. The developed procedure was also useful for the synthesis of Garner’s aldehyde analogues possessing fluorenylmethyloxycarbonyl (Fmoc) or benzyloxycarbonyl (Cbz) protection.
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spelling pubmed-53019082017-02-22 Solution-phase automated synthesis of an α-amino aldehyde as a versatile intermediate Masui, Hisashi Yosugi, Sae Fuse, Shinichiro Takahashi, Takashi Beilstein J Org Chem Letter A solution-phase automated synthesis of the versatile synthetic intermediate, Garner’s aldehyde, was demonstrated. tert-Butoxycarbonyl (Boc) protection, acetal formation, and reduction of the ester to the corresponding aldehyde were performed utilizing our originally developed automated synthesizer, ChemKonzert. The developed procedure was also useful for the synthesis of Garner’s aldehyde analogues possessing fluorenylmethyloxycarbonyl (Fmoc) or benzyloxycarbonyl (Cbz) protection. Beilstein-Institut 2017-01-17 /pmc/articles/PMC5301908/ /pubmed/28228851 http://dx.doi.org/10.3762/bjoc.13.13 Text en Copyright © 2017, Masui 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 Letter
Masui, Hisashi
Yosugi, Sae
Fuse, Shinichiro
Takahashi, Takashi
Solution-phase automated synthesis of an α-amino aldehyde as a versatile intermediate
title Solution-phase automated synthesis of an α-amino aldehyde as a versatile intermediate
title_full Solution-phase automated synthesis of an α-amino aldehyde as a versatile intermediate
title_fullStr Solution-phase automated synthesis of an α-amino aldehyde as a versatile intermediate
title_full_unstemmed Solution-phase automated synthesis of an α-amino aldehyde as a versatile intermediate
title_short Solution-phase automated synthesis of an α-amino aldehyde as a versatile intermediate
title_sort solution-phase automated synthesis of an α-amino aldehyde as a versatile intermediate
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5301908/
https://www.ncbi.nlm.nih.gov/pubmed/28228851
http://dx.doi.org/10.3762/bjoc.13.13
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AT fuseshinichiro solutionphaseautomatedsynthesisofanaaminoaldehydeasaversatileintermediate
AT takahashitakashi solutionphaseautomatedsynthesisofanaaminoaldehydeasaversatileintermediate

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