Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrates
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, 43-48Publisher:
- Freund Publishing House Ltd, London
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Institution/Community
PharmacyTY - 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 - https://hdl.handle.net/21.15107/rcub_farfar_289 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 = "https://hdl.handle.net/21.15107/rcub_farfar_289" }
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. https://hdl.handle.net/21.15107/rcub_farfar_289
Tokić-Vujošević Z, Ceković Z. Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrates. in Heterocyclic Communications. 2001;7(1):43-48. https://hdl.handle.net/21.15107/rcub_farfar_289 .
Tokić-Vujošević, Zorana, Ceković, Z, "Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrates" in Heterocyclic Communications, 7, no. 1 (2001):43-48, https://hdl.handle.net/21.15107/rcub_farfar_289 .