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 |
| Aporte de: |
| Sumario: | 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. |
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