Journal article
A highly stereoselective synthesis of 1-amino-2,5-anhydro-1-deoxyhexitols via 2-trifluoromethyl-oxazolinium intermediates
A series of 1-amino-2,5-anhydro-1-deoxyhexitols, namely derivatives of 1-amino-2,5-anhydro-1-deoxy-D-glucitol, -D-mannitol and D-talitol was prepared from the corresponding 1,3-dideoxy-1-trifluoroacetamido-D-ribo-hexitol and 1-deoxy-1-trifluoroacetamido-L-rhamnitol which both gave the expected C-2 inverted anhydrides.
The reaction mechanism involves 2-trifluoromethyl-oxazolinium intermediates, which further undergo intramolecular attack of HO-5 at C-2 with inversion of the configuration. The reaction is stereospecific and highly regioselective. The crystal structure of 1-amino-2,5-anhydro-1-deoxy-D-glucitol hydrochloride is presented.
Language: | English |
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Year: | 1997 |
Pages: | 261-272 |
ISSN: | 1873426x and 00086215 |
Types: | Journal article |
DOI: | 10.1016/S0008-6215(96)00278-9 |