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Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrates

Authorized Users Only
2001
Authors
Tokić-Vujošević, Zorana
Ceković, Z
Article (Published version)
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Abstract
A synthesis of diastereomeric (7R) 7-endo-nitrooxy-3-oxo-2,5,9-trioxabicyclo[4.3.0]nonane (4b) and (7S) 7-exo-nitrooxy-3-oxo-2,5,9-trioxabicyclo[4.3.0] (7b) is described using D-glucitol as a starting compound. Bicyclic delta -lactones 4 and 7 are obtained in the reaction of 1,4-3,6-dianhydro-2-keto-D-glucitol-5-acylates 3 and 1,4-3, 6-dianhydro-5-keto-D-glucitol-2-acylates 6 with m-chloroperbenzoic acid. Hydrolysis of lactones 4b and 7b and subsequent esterification afforded the corresponding stereoisomeric (3R,4R) methyl (2-acetoxy-4-nitrooxytetrahydrofuran-3-yloxy)-acetate 10 and (3R,4S) isomer 12, respectively.
Source:
Heterocyclic Communications, 2001, 7, 1, 43-48
Publisher:
  • Freund Publishing House Ltd, London

ISSN: 0793-0283

WoS: 000168508300007

Scopus: 2-s2.0-0009761453
[ Google Scholar ]
4
3
URI
https://farfar.pharmacy.bg.ac.rs/handle/123456789/289
Collections
  • Radovi istraživača / Researchers’ publications
Institution/Community
Pharmacy
TY  - JOUR
AU  - Tokić-Vujošević, Zorana
AU  - Ceković, Z
PY  - 2001
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/289
AB  - A synthesis of diastereomeric (7R) 7-endo-nitrooxy-3-oxo-2,5,9-trioxabicyclo[4.3.0]nonane (4b) and (7S) 7-exo-nitrooxy-3-oxo-2,5,9-trioxabicyclo[4.3.0] (7b) is described using D-glucitol as a starting compound. Bicyclic delta -lactones 4 and 7 are obtained in the reaction of 1,4-3,6-dianhydro-2-keto-D-glucitol-5-acylates 3 and 1,4-3, 6-dianhydro-5-keto-D-glucitol-2-acylates 6 with m-chloroperbenzoic acid. Hydrolysis of lactones 4b and 7b and subsequent esterification afforded the corresponding stereoisomeric (3R,4R) methyl (2-acetoxy-4-nitrooxytetrahydrofuran-3-yloxy)-acetate 10 and (3R,4S) isomer 12, respectively.
PB  - Freund Publishing House Ltd, London
T2  - Heterocyclic Communications
T1  - Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrates
VL  - 7
IS  - 1
SP  - 43
EP  - 48
UR  - conv_1308
ER  - 
@article{
author = "Tokić-Vujošević, Zorana and Ceković, Z",
year = "2001",
abstract = "A synthesis of diastereomeric (7R) 7-endo-nitrooxy-3-oxo-2,5,9-trioxabicyclo[4.3.0]nonane (4b) and (7S) 7-exo-nitrooxy-3-oxo-2,5,9-trioxabicyclo[4.3.0] (7b) is described using D-glucitol as a starting compound. Bicyclic delta -lactones 4 and 7 are obtained in the reaction of 1,4-3,6-dianhydro-2-keto-D-glucitol-5-acylates 3 and 1,4-3, 6-dianhydro-5-keto-D-glucitol-2-acylates 6 with m-chloroperbenzoic acid. Hydrolysis of lactones 4b and 7b and subsequent esterification afforded the corresponding stereoisomeric (3R,4R) methyl (2-acetoxy-4-nitrooxytetrahydrofuran-3-yloxy)-acetate 10 and (3R,4S) isomer 12, respectively.",
publisher = "Freund Publishing House Ltd, London",
journal = "Heterocyclic Communications",
title = "Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrates",
volume = "7",
number = "1",
pages = "43-48",
url = "conv_1308"
}
Tokić-Vujošević, Z.,& Ceković, Z.. (2001). Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrates. in Heterocyclic Communications
Freund Publishing House Ltd, London., 7(1), 43-48.
conv_1308
Tokić-Vujošević Z, Ceković Z. Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrates. in Heterocyclic Communications. 2001;7(1):43-48.
conv_1308 .
Tokić-Vujošević, Zorana, Ceković, Z, "Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrates" in Heterocyclic Communications, 7, no. 1 (2001):43-48,
conv_1308 .

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