About: Cross-Coupling Reaction of Saccharide-Based Alkenyl Boronic Acids with Aryl Halides: The Synthesis of Bergenin     Goto   Sponge   NotDistinct   Permalink

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Description
  • A convenient synthetic pathway enabling D-glucal and D-galactal pinacol boronates to be prepared in good isolated yields was achieved. Both pinacol boronates were tested in a series of cross-coupling reactions under Suzuki-Miyaura cross-coupling conditions to obtain the corresponding aryl, heteroaryl, and alkenyl derivatives in high isolated yields. This methodology was applied to the formal synthesis of the glucopyranoside moiety of papulacandinD and the first total synthesis of bergenin.
  • A convenient synthetic pathway enabling D-glucal and D-galactal pinacol boronates to be prepared in good isolated yields was achieved. Both pinacol boronates were tested in a series of cross-coupling reactions under Suzuki-Miyaura cross-coupling conditions to obtain the corresponding aryl, heteroaryl, and alkenyl derivatives in high isolated yields. This methodology was applied to the formal synthesis of the glucopyranoside moiety of papulacandinD and the first total synthesis of bergenin. (en)
Title
  • Cross-Coupling Reaction of Saccharide-Based Alkenyl Boronic Acids with Aryl Halides: The Synthesis of Bergenin
  • Cross-Coupling Reaction of Saccharide-Based Alkenyl Boronic Acids with Aryl Halides: The Synthesis of Bergenin (en)
skos:prefLabel
  • Cross-Coupling Reaction of Saccharide-Based Alkenyl Boronic Acids with Aryl Halides: The Synthesis of Bergenin
  • Cross-Coupling Reaction of Saccharide-Based Alkenyl Boronic Acids with Aryl Halides: The Synthesis of Bergenin (en)
skos:notation
  • RIV/00216208:11310/14:10281056!RIV15-MSM-11310___
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • I, P(GA13-15915S)
http://linked.open...iv/cisloPeriodika
  • 15
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
http://linked.open.../riv/druhVysledku
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  • 9248
http://linked.open...ai/riv/idVysledku
  • RIV/00216208:11310/14:10281056
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  • synthetic methods; protecting groups; natural products; glycosides; CC coupling (en)
http://linked.open.../riv/klicoveSlovo
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  • DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV
  • [F161BF481EE0]
http://linked.open...i/riv/nazevZdroje
  • Chemistry - A European Journal
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http://linked.open...ichTvurcuVysledku
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http://linked.open...vavai/riv/projekt
http://linked.open...UplatneniVysledku
http://linked.open...v/svazekPeriodika
  • 20
http://linked.open...iv/tvurceVysledku
  • Kotora, Martin
  • Pohl, Radek
  • Parkan, Kamil
http://linked.open...ain/vavai/riv/wos
  • 000333632800029
issn
  • 0947-6539
number of pages
http://bibframe.org/vocab/doi
  • 10.1002/chem.201304304
http://localhost/t...ganizacniJednotka
  • 11310
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