Expeditious oligosaccharide synthesis via selective, semi-orthogonal, and orthogonal activation

Traditional strategies for oligosaccharide synthesis often require extensive protecting and/or leaving group manipulations between each glycosylation step, thereby increasing the total number of synthetic steps while decreasing the efficiency of the synthesis. In contrast, expeditious strategies all...

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Veröffentlicht in:Carbohydrate research 2011-09, Vol.346 (12), p.1371-1388
Hauptverfasser: Kaeothip, Sophon, Demchenko, Alexei V.
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description Traditional strategies for oligosaccharide synthesis often require extensive protecting and/or leaving group manipulations between each glycosylation step, thereby increasing the total number of synthetic steps while decreasing the efficiency of the synthesis. In contrast, expeditious strategies allow for the rapid chemical synthesis of complex carbohydrates by minimizing extraneous chemical manipulations. Oligosaccharide synthesis by selective activation of one leaving group over another is one such expeditious strategy. Herein, the significant improvements that have recently emerged in the area of the selective activation are discussed. The development of orthogonal strategy further expands the scope of the selective activation methodology. Surveyed in this article, are representative examples wherein these excellent innovations have been applied to the synthesis of various oligosaccharide sequences.
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source MEDLINE; ScienceDirect Journals (5 years ago - present)
subjects Acetals - chemistry
Acylation
Carbohydrate Conformation
Carbohydrate Sequence
Chemistry, Organic - methods
Fluorides - chemistry
Glycomics
Glycosides - chemical synthesis
Glycosylation
Halogens - chemistry
Heparin - analogs & derivatives
Heparin - chemical synthesis
Imidoesters - chemistry
Ionic Liquids - chemistry
Molecular Sequence Data
Oligosaccharides
Oligosaccharides - chemical synthesis
Orthogonality
Selective activation
Strategy
Sulfoxides - chemistry
synthesis
Thiocyanates - chemistry
title Expeditious oligosaccharide synthesis via selective, semi-orthogonal, and orthogonal activation
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