5847-19-8

Upstream product

• 53286-46-7 (Z)-3β-tosyloxy-5,10-secocholest-1(10)-en-5-one 

Downstream Products

• 5847-17-6 (Z)-3α-acetoxy-5,10-secocholest1(10)-en-5-one 
• 53286-46-7 (Z)-3α-tosyloxy-5,10-secocholest-1(10)-en-5-one 
• 5847-17-6 (Z)-3β-acetoxy-5,10-secocholest1(10)-en-5-one 
• 53286-46-7 (Z)-3β-tosyloxy-5,10-secocholest-1(10)-en-5-one 

Relevant academic research and scientific papers

Synthesis, Structure, and Reactions of Secosteroids containing a Medium-sized Ring. Part 17. Structure-Reactivity Relationship in the Solvolysis of 5,10-Secosteroidal 3-Tosylates

Kinetic measurements of the solvolysis of (Z)-3α- and (Z)-3β-, and (E)-3α- and (E)-3β-tosyloxy-5,10-secocholest-1(10)-en-5-ones in buffered aqueous acetone (90 : 10 v/v) reveal that the (Z)-3α, (E)-3α-, and (E)-3β-tosylates are solvolysed according to a first-order rate law (the relative rates being ca. 1 : 3 : 8), while the (Z)-3β-ester, under the same conditions, reacts at a much slower rate by a complex mechanism, the kinetics of which are best approximated by a second-order law.These data and product analysis indicate that the former three esters are solvolysed with considerable double bond participation , and that this interaction is unimportant for the (Z)-3β-tosylate.On the basis of conformational analysis of the starting tosylates and stereoelectronic requirements for homoallylic interaction, a possible mechanistic pathway for these solvolyses is proposed.