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Peracids oxidation of cholesta-5,8-dien-3β-yl acetate

Oksidacija holesta-5,8-dien-3β-il acetata sa perkiselinama

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Authors
Dabović, Milan
Petrović, Ivanka J.
Krstić, Natalija
Lorenc, Ljubinka
Article (Published version)
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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.
Keywords:
cholesta-5,8-dien-3β-yl acetate / peracid oxidations / steroidal epoxides / reactivity of
Source:
Journal of the Serbian Chemical Society, 2000, 65, 11, 769-772
Publisher:
  • Serbian Chemical Society
Funding / projects:
  • Project MESTD

ISSN: 0352-5139

[ Google Scholar ]
Handle
https://hdl.handle.net/21.15107/rcub_cer_11
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/11
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
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 .

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