Synthetic Aspects of Aminodeoxy Sugars of Antibiotics

Synthetic Aspects of Aminodeoxy Sugars of Antibiotics by Istvan F. Pelyvas, Claude Monneret, Pal Herczegh.

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 Ch...

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Bibliographic Details
Main Authors: Pelyvas, Istvan F. (Author), Monneret, Claude (Author), Herczegh, Pal (Author)
Corporate Author: SpringerLink (Online service)
Format: eBook
Language:English
Published: Berlin, Heidelberg : Springer Berlin Heidelberg : Imprint: Springer, 1988.
Edition:1st ed. 1988.
Series:Springer eBook Collection.
Subjects:
Biochemistry.
Organic chemistry.
Polymers  .
Pharmacy.
Molecular biology.
Pharmacology.
Electronic resources (E-books)
Online Access:Click to view e-book
Holy Cross Note:Loaded electronically.
Electronic access restricted to members of the Holy Cross Community.
Table of Contents:
  • 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.

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