The synthesis of the diastereomeric nitrate esters (3R,4R)-(2-hydroxy-4-nitrooxytetrahydrofuran-3-yloxy)acetonitrile (5b) and (3R,4S)-(2-hydroxy-4-nitrooxytetrahydrofuran-3-yloxy)acetonitrile (9) was achieved by the Beckmann fragmentation of 1,4:3,6-dianhydro-D-glucitol-5-(or -2-)nitrate-2-(or -5-)ketoximes (4b and 8), respectively. The bicyclic delta -lactams, (1R,6R,7R)-N-methyl-7-endo-nitrooxy-3-oxo-5,9-dioxa-2-azabicy-clo[4.3.0]nonane (15b) and the stereoisomer (1R,6R,7S)-7-exo-nitrooxy-3-oxo-5,9-dioxa-2-azabicyclo[4.3.0]nonane (18b) were prepared by the Beckmann rearrangement of nitrones 14b and 17b, respectively. The stereoisomeric delta -lactams, N-methyl-7-endo-benzoyloxy- (15a) and N-methyl-7-exo-benzoyloxy-3-oxo-5,9-dioxa-2-azabicyclo[4.3.0]nonane (18a) were prepared from the corresponding nitrones 14a and 17a, respectively.
TY - JOUR
AU - Tokić-Vujošević, Zorana
AU - Ceković, Z
PY - 2001
UR - http://farfar.pharmacy.bg.ac.rs/handle/123456789/303
AB - The synthesis of the diastereomeric nitrate esters (3R,4R)-(2-hydroxy-4-nitrooxytetrahydrofuran-3-yloxy)acetonitrile (5b) and (3R,4S)-(2-hydroxy-4-nitrooxytetrahydrofuran-3-yloxy)acetonitrile (9) was achieved by the Beckmann fragmentation of 1,4:3,6-dianhydro-D-glucitol-5-(or -2-)nitrate-2-(or -5-)ketoximes (4b and 8), respectively. The bicyclic delta -lactams, (1R,6R,7R)-N-methyl-7-endo-nitrooxy-3-oxo-5,9-dioxa-2-azabicy-clo[4.3.0]nonane (15b) and the stereoisomer (1R,6R,7S)-7-exo-nitrooxy-3-oxo-5,9-dioxa-2-azabicyclo[4.3.0]nonane (18b) were prepared by the Beckmann rearrangement of nitrones 14b and 17b, respectively. The stereoisomeric delta -lactams, N-methyl-7-endo-benzoyloxy- (15a) and N-methyl-7-exo-benzoyloxy-3-oxo-5,9-dioxa-2-azabicyclo[4.3.0]nonane (18a) were prepared from the corresponding nitrones 14a and 17a, respectively.
PB - Georg Thieme Verlag
T2 - Synthesis
T1 - Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrate II: Bicyclic delta-lactams and tetrahydrofuran derivatives
IS - 13
SP - 2028
EP - 2034
DO - 10.1055/s-2001-17705
ER -
@article{
author = "Tokić-Vujošević, Zorana and Ceković, Z",
year = "2001",
url = "http://farfar.pharmacy.bg.ac.rs/handle/123456789/303",
abstract = "The synthesis of the diastereomeric nitrate esters (3R,4R)-(2-hydroxy-4-nitrooxytetrahydrofuran-3-yloxy)acetonitrile (5b) and (3R,4S)-(2-hydroxy-4-nitrooxytetrahydrofuran-3-yloxy)acetonitrile (9) was achieved by the Beckmann fragmentation of 1,4:3,6-dianhydro-D-glucitol-5-(or -2-)nitrate-2-(or -5-)ketoximes (4b and 8), respectively. The bicyclic delta -lactams, (1R,6R,7R)-N-methyl-7-endo-nitrooxy-3-oxo-5,9-dioxa-2-azabicy-clo[4.3.0]nonane (15b) and the stereoisomer (1R,6R,7S)-7-exo-nitrooxy-3-oxo-5,9-dioxa-2-azabicyclo[4.3.0]nonane (18b) were prepared by the Beckmann rearrangement of nitrones 14b and 17b, respectively. The stereoisomeric delta -lactams, N-methyl-7-endo-benzoyloxy- (15a) and N-methyl-7-exo-benzoyloxy-3-oxo-5,9-dioxa-2-azabicyclo[4.3.0]nonane (18a) were prepared from the corresponding nitrones 14a and 17a, respectively.",
publisher = "Georg Thieme Verlag",
journal = "Synthesis",
title = "Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrate II: Bicyclic delta-lactams and tetrahydrofuran derivatives",
number = "13",
pages = "2028-2034",
doi = "10.1055/s-2001-17705"
}
Tokić-Vujošević, Z.,& Ceković, Z. (2001). Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrate II: Bicyclic delta-lactams and tetrahydrofuran derivatives.
Synthesis
Georg Thieme Verlag.(13), 2028-2034.
https://doi.org/10.1055/s-2001-17705
Tokić-Vujošević Z, Ceković Z. Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrate II: Bicyclic delta-lactams and tetrahydrofuran derivatives. Synthesis. 2001;(13):2028-2034
Tokić-Vujošević Zorana, Ceković Z, "Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrate II: Bicyclic delta-lactams and tetrahydrofuran derivatives" Synthesis, no. 13 (2001):2028-2034,
https://doi.org/10.1055/s-2001-17705 .
