A unified strategy for the synthesis of aldohexoses by boronate assisted assembly of CH(2)X(2) derived C(1)-building blocks

A synthetic strategy for all aldohexoses with individually addressable protecting groups from dihalomethane C(1)-units is reported. The underlying synthesis of C(6)-sugar alcohols relies on three consecutive Matteson sequences, vinylation and bishydroxylation. Erythro and threo isomers have been rea...

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Detalles Bibliográficos
Autores principales: Kirupakaran, Sujenth, Arago, Glib, Hirschhäuser, Christoph
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10510816/
https://www.ncbi.nlm.nih.gov/pubmed/37736647
http://dx.doi.org/10.1039/d3sc03778a
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author Kirupakaran, Sujenth
Arago, Glib
Hirschhäuser, Christoph
author_facet Kirupakaran, Sujenth
Arago, Glib
Hirschhäuser, Christoph
author_sort Kirupakaran, Sujenth
collection PubMed
description A synthetic strategy for all aldohexoses with individually addressable protecting groups from dihalomethane C(1)-units is reported. The underlying synthesis of C(6)-sugar alcohols relies on three consecutive Matteson sequences, vinylation and bishydroxylation. Erythro and threo isomers have been realized for every glycol motif by strategic variation of the sequence.
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spelling pubmed-105108162023-09-21 A unified strategy for the synthesis of aldohexoses by boronate assisted assembly of CH(2)X(2) derived C(1)-building blocks Kirupakaran, Sujenth Arago, Glib Hirschhäuser, Christoph Chem Sci Chemistry A synthetic strategy for all aldohexoses with individually addressable protecting groups from dihalomethane C(1)-units is reported. The underlying synthesis of C(6)-sugar alcohols relies on three consecutive Matteson sequences, vinylation and bishydroxylation. Erythro and threo isomers have been realized for every glycol motif by strategic variation of the sequence. The Royal Society of Chemistry 2023-09-04 /pmc/articles/PMC10510816/ /pubmed/37736647 http://dx.doi.org/10.1039/d3sc03778a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Kirupakaran, Sujenth
Arago, Glib
Hirschhäuser, Christoph
A unified strategy for the synthesis of aldohexoses by boronate assisted assembly of CH(2)X(2) derived C(1)-building blocks
title A unified strategy for the synthesis of aldohexoses by boronate assisted assembly of CH(2)X(2) derived C(1)-building blocks
title_full A unified strategy for the synthesis of aldohexoses by boronate assisted assembly of CH(2)X(2) derived C(1)-building blocks
title_fullStr A unified strategy for the synthesis of aldohexoses by boronate assisted assembly of CH(2)X(2) derived C(1)-building blocks
title_full_unstemmed A unified strategy for the synthesis of aldohexoses by boronate assisted assembly of CH(2)X(2) derived C(1)-building blocks
title_short A unified strategy for the synthesis of aldohexoses by boronate assisted assembly of CH(2)X(2) derived C(1)-building blocks
title_sort unified strategy for the synthesis of aldohexoses by boronate assisted assembly of ch(2)x(2) derived c(1)-building blocks
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10510816/
https://www.ncbi.nlm.nih.gov/pubmed/37736647
http://dx.doi.org/10.1039/d3sc03778a
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