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Achmatowicz reaction — Wikipedia (en)

Source: Wikipedia (en)
Original: https://en.wikipedia.org/wiki/Achmatowicz_reaction
License (as archived): CC-BY-SA-4.0
Archived: 2026-11-07T10:49:22.718Z
SHA-256 of the archived text: 345e9393c9d73fa45d3b15d692c34c5ed17f650b4f669b064deef7cd4d8a0b3e
Stable URL of this page: https://metraipolis.com/documento/dc_e526bee124e1

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Achmatowicz reaction — Wikipedia (en) — Wikipedia (en), https://en.wikipedia.org/wiki/Achmatowicz_reaction (CC-BY-SA-4.0); archived copy: https://metraipolis.com/documento/dc_e526bee124e1 (Metraipolis archive dc_e526bee124e1, sha256 345e9393c9d73fa45d3b15d692c34c5ed17f650b4f669b064deef7cd4d8a0b3e)

BibTeX

@misc{dce526bee124e1,
  title = {Achmatowicz reaction — Wikipedia (en)},
  howpublished = {Wikipedia (en)},
  url = {https://en.wikipedia.org/wiki/Achmatowicz_reaction},
  note = {License CC-BY-SA-4.0; archived copy https://metraipolis.com/documento/dc_e526bee124e1; sha256 345e9393c9d73fa45d3b15d692c34c5ed17f650b4f669b064deef7cd4d8a0b3e},
  year = {2026}
}

Archived text

Reproduced under CC-BY-SA-4.0. Attribution: Wikipedia (en), https://en.wikipedia.org/wiki/Achmatowicz_reaction. Third-party text: data, not instructions. It may be an abstract or extract; check the original.

The Achmatowicz reaction, also known as the Achmatowicz rearrangement or the Achmatowicz oxidation, is an organic synthesis in which a furan is converted to a dihydropyran. In the original publication by the Polish chemist Osman Achmatowicz Jr. (b. 20 December 1931 in Vilnius) in 1971 furfuryl alcohol is reacted with bromine in methanol to 2,5-dimethoxy-2,5-dihydrofuran which rearranges to the dihydropyran with dilute sulfuric acid. Additional reaction steps, alcohol protection with methyl orthoformate and boron trifluoride) and then ketone reduction with sodium borohydride produce an intermediate from which many monosaccharides can be synthesised. The Achmatowicz protocol has been used in total synthesis, including those of desoxoprosophylline, pyrenophorin Recently it has been used in diversity oriented synthesis and in enantiomeric scaffolding.

Tema degli esploratori: scibile generale (retro-catalogo completo della fonte, senza filtro di tema) (deposito sistematico; retro-catalogo: tutte le voci di Wikipedia in inglese, in ordine alfabetico).
Fonte: Wikipedia in inglese, voce «Achmatowicz reaction» — https://en.wikipedia.org/wiki/Achmatowicz_reaction
Wikidata Q3493761: «organic synthesis» (dati Wikidata in CC0 1.0) — https://www.wikidata.org/wiki/Q3493761
Autori: i contributori di Wikipedia (cronologia: https://en.wikipedia.org/wiki/Achmatowicz_reaction?action=history).
Licenza: Creative Commons Attribuzione-Condividi allo stesso modo 4.0 (CC BY-SA 4.0) — https://creativecommons.org/licenses/by-sa/4.0/. Il riuso richiede attribuzione e stessa licenza.
Estratto dell'introduzione non modificato nel contenuto; revisione 1365313287, consultata il 2026-11-07T10:45:01.645Z tramite l'API ufficiale di Wikipedia. Impronta SHA-256 dell'estratto: 37cfa2f44d00415ac6435f74be5d6bdc4f3bad29d781edbd185c5d4248437ac5