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...
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1997
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v303_n4_p417_Cirelli http://hdl.handle.net/20.500.12110/paper_00086215_v303_n4_p417_Cirelli |
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paper:paper_00086215_v303_n4_p417_Cirelli2023-06-08T14:32:35Z Synthesis of thromboxane A2 models from glucose 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. 1997 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v303_n4_p417_Cirelli http://hdl.handle.net/20.500.12110/paper_00086215_v303_n4_p417_Cirelli |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
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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 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. |
| 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 |
| publishDate |
1997 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v303_n4_p417_Cirelli http://hdl.handle.net/20.500.12110/paper_00086215_v303_n4_p417_Cirelli |
| _version_ |
1768545308516548608 |