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.
TY - JOUR
AU - Tokić-Vujošević, Zorana
AU - Ceković, Z
PY - 2001
UR - http://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
ER -
@article{
author = "Tokić-Vujošević, Zorana and Ceković, Z",
year = "2001",
url = "http://farfar.pharmacy.bg.ac.rs/handle/123456789/289",
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"
}
Tokić-Vujošević, Z.,& Ceković, Z. (2001). Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrates.
Heterocyclic Communications
Freund Publishing House Ltd, London., 7(1), 43-48.
Tokić-Vujošević Z, Ceković Z. Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrates. Heterocyclic Communications. 2001;7(1):43-48
Tokić-Vujošević Zorana, Ceković Z, "Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrates" Heterocyclic Communications, 7, no. 1 (2001):43-48
