Istvan F. Pelyvas, Claude Monneret, Pal Herczegh

Synthetic Aspects of Aminodeoxy Sugars of Antibiotics (eBook, PDF)

• Format: PDF

Produktbeschreibung

The synthetic chemistry of carbohydrates has advanced at a scarcely equalled rate in the last 25 years, due to the great interest of biologically active natural products coritaining sugar moieties. It suffices to note that in the review by J. D. Dutcher appearing in "Advances in Carbohydrate Chemistry" vol. 18, 1963, only the structures of less than ten aminodeoxy sugars were reported. This book deals exclusively with a single class of carbohydrates, namely the aminodeoxy sugars of antibiotics, the most popular of which is probably daunosamine, a compound for which more than 20 different synthetic approaches have been reported in the literature since the publication of its structure in 1964. No compound in the 3-amino-2-deoxY-L-hexose series had been prepared by chemical synthesis when we started our synthetic work in this field in 1972 on the wave of the successful therapeutic applications of adriamycin. The compounds with xylo stereochemistry were unknown even in the more easily accessible D-series. The size of this book documents the rapid development of the field. I wish to add that the improvements of chemical methodology reported in. the volume outspan the specific field and are of importance in the design of synthetic approaches to other carbohydrate structures. These also include compounds involved in chemical interactions of great biological interest, but hitherto un explained at the molecular level, such as those related with cell recognition, adhesiveness and differentiation.

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Produktdetails

• Verlag: Springer Berlin Heidelberg
• Seitenzahl: 244
• Erscheinungstermin: 6. Dezember 2012
• Englisch
• ISBN-13: 9783642733994
• Artikelnr.: 53389650

Inhaltsangabe

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.