About: Conversion of Thebaine to Oripavine and Other Useful Intermediates for the Semisynthesis of Opiate-Derived Agents: Synthesis of Hydromorphone     Goto   Sponge   Distinct   Permalink

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Description
  • Thebaine was converted to oripavine in three steps by employing two different modes of protection of the diene moiety; as an iron tricarbonyl complex and as a Diels-Alder adduct with thioformyl cyanide. The two C-ring-protected thebaine derivatives were subjected to 3-O-demethylation by four different protocols, providing oripavine derivatives, which yielded oripavine after deprotection. Oripavine was then converted to hydromorphone by a three-step process of ketalization, hydrogenation, and deprotection, without the isolation of intermediates.
  • Thebaine was converted to oripavine in three steps by employing two different modes of protection of the diene moiety; as an iron tricarbonyl complex and as a Diels-Alder adduct with thioformyl cyanide. The two C-ring-protected thebaine derivatives were subjected to 3-O-demethylation by four different protocols, providing oripavine derivatives, which yielded oripavine after deprotection. Oripavine was then converted to hydromorphone by a three-step process of ketalization, hydrogenation, and deprotection, without the isolation of intermediates. (en)
Title
  • Conversion of Thebaine to Oripavine and Other Useful Intermediates for the Semisynthesis of Opiate-Derived Agents: Synthesis of Hydromorphone
  • Conversion of Thebaine to Oripavine and Other Useful Intermediates for the Semisynthesis of Opiate-Derived Agents: Synthesis of Hydromorphone (en)
skos:prefLabel
  • Conversion of Thebaine to Oripavine and Other Useful Intermediates for the Semisynthesis of Opiate-Derived Agents: Synthesis of Hydromorphone
  • Conversion of Thebaine to Oripavine and Other Useful Intermediates for the Semisynthesis of Opiate-Derived Agents: Synthesis of Hydromorphone (en)
skos:notation
  • RIV/00216208:11310/14:10285972!RIV15-MSM-11310___
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • I
http://linked.open...iv/cisloPeriodika
  • 11-12
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
http://linked.open.../riv/druhVysledku
http://linked.open...iv/duvernostUdaju
http://linked.open...titaPredkladatele
http://linked.open...dnocenehoVysledku
  • 8910
http://linked.open...ai/riv/idVysledku
  • RIV/00216208:11310/14:10285972
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • thebaine O-demethylation; protecting groups; oripavine synthesis; natural products; iron-diene complexes; hydromorphone synthesis; hetero-Diels-Alder cycloaddition; alkaloids (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV
  • [27241209F2DA]
http://linked.open...i/riv/nazevZdroje
  • Advanced Synthesis and Catalysis
http://linked.open...in/vavai/riv/obor
http://linked.open...ichTvurcuVysledku
http://linked.open...cetTvurcuVysledku
http://linked.open...UplatneniVysledku
http://linked.open...v/svazekPeriodika
  • 356
http://linked.open...iv/tvurceVysledku
  • Šnajdr, Ivan
  • Machara, Aleš
  • Cox, D. Phillip
  • Endoma-Arias, Mary Ann A.
  • Hudlický, Tomáš
  • Murphy, Brennan
  • Stamatatos, Theocharis C.
http://linked.open...ain/vavai/riv/wos
  • 000340567100033
issn
  • 1615-4150
number of pages
http://bibframe.org/vocab/doi
  • 10.1002/adsc.201400445
http://localhost/t...ganizacniJednotka
  • 11310
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