Expoxidation of cholesta-5,8-dien-3β-yl acetate (1) with peracids takes place preferentially at the more highly substituted Δ8-olefinic double bond to give: (a) with monoperphthalic acid, 8α,9α-epoxycholest-5-en-3β-yl acetate (2) (in 39 % yield) and 9α-hydroxy-5α,6α-epoxycholest-8(14)-en-3β-yl acetate (3) (in 30 % yield); and (b) with m-chloroperbenzoic acid, the 8α,9α-epoxide 2 (64 %) and 5α,6α-epoxy derivative 3 (20 %). Some chemical transformations of the obtained epoxides are described.
Epoksidacija holesta-5,8-dien-3β-il acetata (1) sa perkiselinama prvenstveno se odvija na više supstituisanoj Δ8-olefinskoj dvoguboj vezi pri čemu se dobija: (a) sa monoperftalnom kiselinom, 8α,9α-epoksiholest-5-en-3β-il acetat (2) (u prenosu od 39 %) i 9α-hidroksi-5α,6α-epoksiholest-8(14)-en-3β-il acetat (3) (u prenosu od 30 %); i (b) sa m-hlorperbenzoevom kiselinom, 8α,9α-epoksid 2 (u prenosu od 64 %) i 5α,6α-epoksi derivat 3 (u prenosu od 20 %). Opisane su i neke hemijske transformacije dobijenih epoksida.
TY - JOUR
AU - Dabović, Milan
AU - Petrović, Ivanka J.
AU - Krstić, Natalija
AU - Lorenc, Ljubinka
PY - 2000
UR - https://cer.ihtm.bg.ac.rs/handle/123456789/11
AB - Expoxidation of cholesta-5,8-dien-3β-yl acetate (1) with peracids takes place preferentially at the more highly substituted Δ8-olefinic double bond to give: (a) with monoperphthalic acid, 8α,9α-epoxycholest-5-en-3β-yl acetate (2) (in 39 % yield) and 9α-hydroxy-5α,6α-epoxycholest-8(14)-en-3β-yl acetate (3) (in 30 % yield); and (b) with m-chloroperbenzoic acid, the 8α,9α-epoxide 2 (64 %) and 5α,6α-epoxy derivative 3 (20 %). Some chemical transformations of the obtained epoxides are described.
AB - Epoksidacija holesta-5,8-dien-3β-il acetata (1) sa perkiselinama prvenstveno se odvija na više supstituisanoj Δ8-olefinskoj dvoguboj vezi pri čemu se dobija: (a) sa monoperftalnom kiselinom, 8α,9α-epoksiholest-5-en-3β-il acetat (2) (u prenosu od 39 %) i 9α-hidroksi-5α,6α-epoksiholest-8(14)-en-3β-il acetat (3) (u prenosu od 30 %); i (b) sa m-hlorperbenzoevom kiselinom, 8α,9α-epoksid 2 (u prenosu od 64 %) i 5α,6α-epoksi derivat 3 (u prenosu od 20 %). Opisane su i neke hemijske transformacije dobijenih epoksida.
PB - Serbian Chemical Society
T2 - Journal of the Serbian Chemical Society
T1 - Peracids oxidation of cholesta-5,8-dien-3β-yl acetate
T1 - Oksidacija holesta-5,8-dien-3β-il acetata sa perkiselinama
VL - 65
IS - 11
SP - 769
EP - 772
UR - https://hdl.handle.net/21.15107/rcub_cer_11
ER -
@article{
author = "Dabović, Milan and Petrović, Ivanka J. and Krstić, Natalija and Lorenc, Ljubinka",
year = "2000",
abstract = "Expoxidation of cholesta-5,8-dien-3β-yl acetate (1) with peracids takes place preferentially at the more highly substituted Δ8-olefinic double bond to give: (a) with monoperphthalic acid, 8α,9α-epoxycholest-5-en-3β-yl acetate (2) (in 39 % yield) and 9α-hydroxy-5α,6α-epoxycholest-8(14)-en-3β-yl acetate (3) (in 30 % yield); and (b) with m-chloroperbenzoic acid, the 8α,9α-epoxide 2 (64 %) and 5α,6α-epoxy derivative 3 (20 %). Some chemical transformations of the obtained epoxides are described., Epoksidacija holesta-5,8-dien-3β-il acetata (1) sa perkiselinama prvenstveno se odvija na više supstituisanoj Δ8-olefinskoj dvoguboj vezi pri čemu se dobija: (a) sa monoperftalnom kiselinom, 8α,9α-epoksiholest-5-en-3β-il acetat (2) (u prenosu od 39 %) i 9α-hidroksi-5α,6α-epoksiholest-8(14)-en-3β-il acetat (3) (u prenosu od 30 %); i (b) sa m-hlorperbenzoevom kiselinom, 8α,9α-epoksid 2 (u prenosu od 64 %) i 5α,6α-epoksi derivat 3 (u prenosu od 20 %). Opisane su i neke hemijske transformacije dobijenih epoksida.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Peracids oxidation of cholesta-5,8-dien-3β-yl acetate, Oksidacija holesta-5,8-dien-3β-il acetata sa perkiselinama",
volume = "65",
number = "11",
pages = "769-772",
url = "https://hdl.handle.net/21.15107/rcub_cer_11"
}
Dabović, M., Petrović, I. J., Krstić, N.,& Lorenc, L.. (2000). Peracids oxidation of cholesta-5,8-dien-3β-yl acetate. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 65(11), 769-772.
https://hdl.handle.net/21.15107/rcub_cer_11
Dabović M, Petrović IJ, Krstić N, Lorenc L. Peracids oxidation of cholesta-5,8-dien-3β-yl acetate. in Journal of the Serbian Chemical Society. 2000;65(11):769-772.
https://hdl.handle.net/21.15107/rcub_cer_11 .
Dabović, Milan, Petrović, Ivanka J., Krstić, Natalija, Lorenc, Ljubinka, "Peracids oxidation of cholesta-5,8-dien-3β-yl acetate" in Journal of the Serbian Chemical Society, 65, no. 11 (2000):769-772,
https://hdl.handle.net/21.15107/rcub_cer_11 .
