Synthetic Aspects of Aminodeoxy Sugars of Antibiotics

1. Introduction.- 2. Synthesis of 3-Amino-2,3,6-Trideoxyhexoses from Carbohydrates.- 2.1 Synthesis of 2-deoxyhexose derivatives.- 2.2 Introduction of the C-3 amino function into mono- and dideoxyhexose derivatives.- 2.3 Simultaneous generation of the C-3 amino and C-2 deoxy functions.- 2.5 Methodologies for the preparation of 3-C-methyl branched-chain 3-amino- and 3-nitrosugars of antibiotic substances.- 2.6 Subsequent generation of the 2-deoxy functionality of unbranched- and branched-chain 3-aminosugars.- 2.7 Synthetic strategies for the preparation of the 6-deoxy analogs of 3-amino-3-deoxyhexopyranosides.- 2.8 Interconversion of 3-amino-2,3-dideoxy- and 3-amino- 2,3,6-trideoxyhexose derivatives by means of the inversion of the configuration at carbon C-4.- 3. Synthesis of 3-Amino-2,3,6-Trideoxyhexoses by Using Non-carbohydrate Precursors.- 3.1 Synthesis of 3-amino-2,3,6-trideoxyhexoses from six-carbon substrates.- 3.2 Synthesis of 3-amino-2,3,6-trideoxyhexoses from chiral and achiral precursors by means of carbon-carbon bond formation reactions.- 4. Miscellaneous Functionalized Derivatives of 3-Amino-3-Deoxyhexoses of Antibiotics and Their Conversion into Other Organic Substances.- 4.1 Thio-, nitrogen-and C-glycosides of 3-amino-2,3,6-trideoxyhexoses.- 4.2 N-Substituted derivatives of daunosamine-type aminodeoxy hexoses.- 4.3 4-Deoxy-, C-4 branched-chain and other C-4 substituted derivatives of 3-amino-2,3,6-trideoxyhexoses.- 4.4 Furanose-ring analogs of 3-amino-2,3,6-trideoxyhexoses.- 4.5 Synthesis of the 6-azido- and 6-amino derivatives of 3-amino-di- and trideoxyhexoses.- 4.6 Synthesis of the uronic acid derivatives of 3-amino-di- and trideoxyhexoses.- 4.7 Conversion of 3-amino- and 3-azido-2,3,6-trideoxyhexose derivatives into carbocyclic compounds.- 5. Concluding Remarks.- Note Added in Proof.- References.