- Rapid conversion of spirostans into furostan skeletons at room temperature.
Rapid conversion of spirostans into furostan skeletons at room temperature.
Steroids (2011-11-09)
Omar Viñas-Bravo, Roxana Martinez-Pascual, José Luis Vega-Baez, Víctor Gómez-Calvario, Jesús Sandoval-Ramírez, Sara Montiel-Smith, Socorro Meza-Reyes, Alejandra López-De Rosas, Mónica Martínez-Montiel, Mayra Reyes, José A Ruiz
PMID22061618
ABSTRACT
We report a facile protocol to obtain 22-substituted furostans and pseudosapogenins in high yields from (25R)- and (25S)-sapogenins. This method involves the treatment of the sapogenin with acetic-trifluoroacetic mixed anhydride and BF(3)·OEt(2) at room temperature, followed by the addition of a nucleophile (H(2)O, MeOH or KSeCN). In the case of 22-hydroxyfurostans, they can be transformed to pseudosapogenins by treatment with p-toluensulfonic acid.
MATERIALS
Product Number
Brand
Product Description
Supelco
Trifluoroacetic anhydride, derivatization grade (GC derivatization), LiChropur™, ≥99.0% (GC)