Synthesis of thromboxane A2 models from glucose
Trans-opening of the 2,3-anhydro-6-deoxy-4-O-methyl-α-D-allopyranoside with lithium bromide yields the altro and gluco regioisomers methyl 2-bromo- 2,6-dideoxy-4-O-methyl-α-D-altropyranoside and methyl 2-bromo-3,6-dideoxy- 4-O-methyl-α-D-glycopyranoside which can be hydrolysed to give the sugar prec...
Guardado en:
| Autores principales: | , , |
|---|---|
| Formato: | JOUR |
| Materias: | |
| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00086215_v303_n4_p417_Cirelli |
| Aporte de: |
| id |
todo:paper_00086215_v303_n4_p417_Cirelli |
|---|---|
| record_format |
dspace |
| spelling |
todo:paper_00086215_v303_n4_p417_Cirelli2023-10-03T14:06:49Z Synthesis of thromboxane A2 models from glucose Cirelli, A.F. Mohn, H. Thiem, J. 1.3-Anhydro-α-D-altropyranoside 2,6- dideoxy 2.6-Dioxabicyclo[3.1.1]heptanes Model compounds Thromboxane glucose pyranoside sugar thromboxane a2 article debromination isomer photolysis priority journal reaction analysis synthesis Trans-opening of the 2,3-anhydro-6-deoxy-4-O-methyl-α-D-allopyranoside with lithium bromide yields the altro and gluco regioisomers methyl 2-bromo- 2,6-dideoxy-4-O-methyl-α-D-altropyranoside and methyl 2-bromo-3,6-dideoxy- 4-O-methyl-α-D-glycopyranoside which can be hydrolysed to give the sugar precursors 2-bromo-2,6-dideoxy-4-O-methyl-α/β-D-altropyranose and 3-bromo- 3,6-dideoxy-4-O-methyl-D-glucopyranose. Under Mitsunobu conditions the altro compound yields the first 1,3-anhydro-altrose derivative. In case of the gluco derivative alkaline treatment does not give a 1,3-anhydro-glucose derivative but the 2,6-dideoxy-altrose via intermediate 2,3-epoxide formation. Methanolysis and reductive debromination under photolytic initiation were studied. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00086215_v303_n4_p417_Cirelli |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
1.3-Anhydro-α-D-altropyranoside 2,6- dideoxy 2.6-Dioxabicyclo[3.1.1]heptanes Model compounds Thromboxane glucose pyranoside sugar thromboxane a2 article debromination isomer photolysis priority journal reaction analysis synthesis |
| spellingShingle |
1.3-Anhydro-α-D-altropyranoside 2,6- dideoxy 2.6-Dioxabicyclo[3.1.1]heptanes Model compounds Thromboxane glucose pyranoside sugar thromboxane a2 article debromination isomer photolysis priority journal reaction analysis synthesis Cirelli, A.F. Mohn, H. Thiem, J. Synthesis of thromboxane A2 models from glucose |
| topic_facet |
1.3-Anhydro-α-D-altropyranoside 2,6- dideoxy 2.6-Dioxabicyclo[3.1.1]heptanes Model compounds Thromboxane glucose pyranoside sugar thromboxane a2 article debromination isomer photolysis priority journal reaction analysis synthesis |
| description |
Trans-opening of the 2,3-anhydro-6-deoxy-4-O-methyl-α-D-allopyranoside with lithium bromide yields the altro and gluco regioisomers methyl 2-bromo- 2,6-dideoxy-4-O-methyl-α-D-altropyranoside and methyl 2-bromo-3,6-dideoxy- 4-O-methyl-α-D-glycopyranoside which can be hydrolysed to give the sugar precursors 2-bromo-2,6-dideoxy-4-O-methyl-α/β-D-altropyranose and 3-bromo- 3,6-dideoxy-4-O-methyl-D-glucopyranose. Under Mitsunobu conditions the altro compound yields the first 1,3-anhydro-altrose derivative. In case of the gluco derivative alkaline treatment does not give a 1,3-anhydro-glucose derivative but the 2,6-dideoxy-altrose via intermediate 2,3-epoxide formation. Methanolysis and reductive debromination under photolytic initiation were studied. |
| format |
JOUR |
| author |
Cirelli, A.F. Mohn, H. Thiem, J. |
| author_facet |
Cirelli, A.F. Mohn, H. Thiem, J. |
| author_sort |
Cirelli, A.F. |
| title |
Synthesis of thromboxane A2 models from glucose |
| title_short |
Synthesis of thromboxane A2 models from glucose |
| title_full |
Synthesis of thromboxane A2 models from glucose |
| title_fullStr |
Synthesis of thromboxane A2 models from glucose |
| title_full_unstemmed |
Synthesis of thromboxane A2 models from glucose |
| title_sort |
synthesis of thromboxane a2 models from glucose |
| url |
http://hdl.handle.net/20.500.12110/paper_00086215_v303_n4_p417_Cirelli |
| work_keys_str_mv |
AT cirelliaf synthesisofthromboxanea2modelsfromglucose AT mohnh synthesisofthromboxanea2modelsfromglucose AT thiemj synthesisofthromboxanea2modelsfromglucose |
| _version_ |
1807314578754764800 |