104530-11-2

Upstream product

• 30414-55-2 methyl 5-methyl-3-oxohexanoate 
• 78424-47-2 tert-Butyl-[(3S,10R,13S,15S,16R)-17-eth-(E)-ylidene-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-20-oxa-cyclopropa[15,16]cyclopenta[a]phenanthren-3-yloxy]-dimethyl-silane 
• 78424-47-2 (17E)-3β-(dimethyl-t-butylsilyloxy)-15β,16β-epoxypregna-5,17(20)-diene 

Relevant academic research and scientific papers

Regio- and stereoselective introduction of 15β-hydroxy group and side chains to steroids by the palladium-catalyzed reaction of 1,3-diene monoepoxide

The Pd-catalyzed reaction of 1,3-diene monoepoxides with carbonucleophiles is applied to the regio- and stereoselective introduction of 15β-hydroxy group and side chains to steroid nuclei. 3β-Hydroxyandrost-5-en-17-one (15) was converted to 15,16β-epoxy-Δ17(20) isoheptylidene steroid 20 and ethylidene steroid 21. The former was subjected to the Pd-catalyzed reaction with dimethyl malonate and then converted to 15β-hydroxycholesterol (29). Similarly, 15β-hydroxyisocholesterol (32) was obtained from the ethylidene steroid 21 using the Pd-catalyzed reaction of methyl 3-oxo-5-methylhexanoate (24) as a key reaction.

PALLADIUM-CATALYZED CHIRALITY TRANSFER OF 1,3-DIENE MONOEPOXIDES AND ITS APPLICATION TO THE SYNTHESIS OF STEROID SIDE CHAINS

The palladium-catalyzed 1,4-addition of nucleophiles to 15β,16β-epoxy-E-Δ17(20)-isoheptylidene steroid 8 and 15β,16β-epoxy-E-Δ17(20)-ethylidene steroid 13 has been studied as a good method for regio- and stereoselective introduction of steroid side chains.