Abstract
Reaction of 3β-methoxymethoxy-5-pregnen-20-one (Ia) with diethyl cyanomethylphosphonate and subsequent removal of the protecting group afforded (20E)-3β-hydroxy-24-norchola-5,20(22)-diene-23-nitrile (IIIa). Besides the analogous derivative IIIb with another double bond in position 14, the fully saturated compounds IIIc and IIId with configuration 5α and 5β, respectively, were prepared similarly. Silver silicate-catalyzed glycosylation of IIIa-IIId with tetra-O-acetyl-α-D-glucopyranosyl bromide gave β-D-glucopyranosides IVa-IVd in 77-89% yield. A parallel series of hemisuccinates VIa-VId was prepared in 64-81% yields by reaction of IIIa-IIId with 2-(trimethylsilyl)ethyl hydrogen butanedioate followed by deblocking with tetrabutylammonium fluoride. The glucoside IVa was prepared also by an alternative reaction pathway starting from 3β-hydroxy-5-pregnen-20-one (VIII). Compound VIII was converted in 80% yield into the glucoside IX which, after protection as the tetra-O-(trimethylsilyl)derivative XII, was treated with diethyl cyanomethylphosphonate.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callMore From: Collection of Czechoslovak Chemical Communications
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
