Reaktion #612473

ord-8a5b830395c34542b8e4bd8391909847

Reaktionsgleichung

CC(=O)O[C@H]1[C@H]2[C@H]([C@@H]3[C@@H](O)[C@@H]4[C@H]([C@H](C)C=C5OC(=O)[C@@](C)(O)[C@@]54C)[C@@]3(C)[C@H]1OC(C)=O)[C@@H](O)C(=O)[C@H]1C[C@@H]3O[C@@H]3[C@H](OC(C)=O)[C@]21C
Taccalonolide B
CC(=O)OC(C)=O
acetic anhydride
c1ccncc1
pyridine
→
CC(=O)O[C@@H]1[C@H]2[C@H]3[C@H]([C@H](OC(C)=O)[C@H](OC(C)=O)[C@]2(C)[C@@H]2[C@@H]1[C@]1(C)C(=C[C@H]2C)OC(=O)[C@@]1(C)O)[C@]1(C)[C@H](C[C@@H]2O[C@@H]2[C@@H]1OC(C)=O)C(=O)[C@@H]3O
taccalonolide A

Edukte

CC(=O)O[C@H]1[C@H]2[C@H]([C@@H]3[C@@H](O)[C@@H]4[C@H]([C@H](C)C=C5OC(=O)[C@@](C)(O)[C@@]54C)[C@@]3(C)[C@H]1OC(C)=O)[C@@H](O)C(=O)[C@H]1C[C@@H]3O[C@@H]3[C@H](OC(C)=O)[C@]21C
Taccalonolide B
CC(=O)OC(C)=O
acetic anhydride
c1ccncc1
pyridine

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe reaction solution was dried in miVac
  2. 2
    Sonstigeseparated

Vorschrift

Taccalonolide B (3 mg) was dissolved in 0.3 mL of acetic anhydride. To this solution, 0.3 mL of anhydrous pyridine was added and was kept at room temperature for 48 h. The reaction solution was dried in miVac and separated using C18 HPLC to yield taccalonolide A and TB-Ac-16.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09340572B2uspto-grants-2016_05