74150-85-9

Upstream product

• 1059-86-5 7-Dehydrocholesteryl acetate 
• 15361-36-1 5,8-epidioxy-5α,8α-cholest-6-en-3β-ol acetate 
• 92594-30-4 (1R,3aR,3bS,5aR,7S,9aR,9bR,11aR)-3b,5a-diformyl-9a,11a-dimethyl-1-(6-methylheptan-2-yl)tetradecahydro-1H-benzo[c]indeno[5,4-e][1,2]dioxin-7-yl acetate 

Relevant academic research and scientific papers

Ozonolysis of bicyclic 1,2-dioxines: Initial scope and mechanistic insights

The ozonolysis of bicyclic 1,2-dioxines was investigated using a variety of 1,4-disubstituted 1,2-dioxines along with a 1,3-dialkyl and steroidal example, with yields ranging from moderate to excellent. Two different pathways were observed upon reaction of the 1,4-disubstituted 1,2-dioxines with ozone; one pathway saw the "expected" results, that is, cleavage of the olefinic moiety with generation of 1,4-dicarbonyl 1,2-dioxines, while the other pathway revealed a previously unobserved rearrangement involving cleavage of the peroxide linkage along with loss of either CO or CO2. Several unsymmetrical ozonolyses were also performed to further investigate the origins of this rearrangement, and initial mechanistic insights into the fragmentation pathways are discussed.

OXIDATIVE CLEAVAGE OF THE DOUBLE BOND OF 7-DEHYDROCHOLESTEROL ACETATE PEROXIDE

Ozonolysis of 7-dehydrocholesterol acetate peroxide is described.The structures of diketone 3 and lactol 4 were confirmed by their LAH reduction to triol 7 and tetraol 9, respectively.Moreover, tetraol 9, tetraol 12 and pentaol 14 were obtained from reduction of ozonation products.It has been established that compounds 3 and 4 are formed as a result of rearrangements of the first detectable product of epidioxy 2 ozonation, namely epidioxydialdehyde 16.