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Beilstein J. Org. Chem. 2021, 17, 1086–1095, doi:10.3762/bjoc.17.85
Graphical Abstract
Scheme 1: Retrosynthetic analysis of the target fluoro analogs.
Scheme 2: Conversion of 1,6-anhydro derivatives into thioglycosides, and a possible mechanism for the formati...
Scheme 3: Deoxyfluorination and O-benzylation of thioglycosides and thioaglycone migration.
Scheme 4: Thioglycoside hydrolysis.
Scheme 5: Synthesis of the target compounds by azide/acetamide conversion and debenzylation.
Beilstein J. Org. Chem. 2016, 12, 750–759, doi:10.3762/bjoc.12.75
Figure 1: Examples of deoxofluorinated hexosamines.
Scheme 1: Retrosynthetic plan.
Scheme 2: Preparation of starting 2-azido compounds. Reagents and conditions: (a) NaN3, NH4Cl, MeOC2H4OH, 79%...
Scheme 3: Preparation of mono and difluoro analogs of 2-azido-2-deoxy-1,6-anhydro-β-D-gluco- and galactopyran...
Scheme 4: Suggested mechanisms for deoxofluorination at C-3 of 1,6-anhydro-β-D-glucohexopyranose derivatives....
Scheme 5: Formation of oxazoline 41 from 19.
Scheme 6: 1-O-Deacetylation of monofluorinated hexosamines. Reagents and conditions: (a) BnNH2, THF, 62%; (b)...