A unified strategy for the synthesis of aldohexoses by boronate assisted assembly of CH2X2 derived C1-building blocks

A synthetic strategy for all aldohexoses with individually addressable protecting groups from dihalomethane C1-units is reported. The underlying synthesis of C6-sugar alcohols relies on three consecutive Matteson sequences, vinylation and bishydroxylation. Erythro and threo isomers have been realize...

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Veröffentlicht in:Chemical science (Cambridge) 2023-09, Vol.14 (36), p.9838-9842
Hauptverfasser: Kirupakaran, Sujenth, Arago, Glib, Hirschhäuser, Christoph
Format: Artikel
Sprache:eng
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Zusammenfassung:A synthetic strategy for all aldohexoses with individually addressable protecting groups from dihalomethane C1-units is reported. The underlying synthesis of C6-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.
ISSN:2041-6520
2041-6539
DOI:10.1039/d3sc03778a