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Solids in which the atoms, ions, or molecules are arranged in a definite repeating pattern are known as crystalline solids. Metals and ionic compounds typically form ordered, crystalline solids. A crystalline solid has a precise melting temperature because each atom or molecule of the same type is held in place with the same forces or energy. Amorphous solids or non-crystalline solids (or, sometimes, glasses) which lack an ordered internal structure and are randomly arranged. Substances that...
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Solid-Phase Synthesis of Thio-oligosaccharides.

Gerd Hummel1, Ole Hindsgaul1

  • 1Department of Chemistry, University of Alberta, Edmonton, AB, T6G 2G2 (Canada), Fax: (+1) 403-492-8231.

Angewandte Chemie (International Ed. in English)
|May 2, 2018
PubMed
Summary

Highly reactive polymer-bound sugar thiolates react with sugar triflates to efficiently produce thio-oligosaccharides. This method avoids protecting groups, simplifying the synthesis of complex carbohydrates.

Keywords:
OligosaccharidesSolid-phase synthesisThio-glycosidesThio-oligosaccharidesThiolates

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Area of Science:

  • Carbohydrate Chemistry
  • Polymer Chemistry
  • Organic Synthesis

Background:

  • Protecting groups are commonly used in carbohydrate synthesis but add steps and complexity.
  • Developing efficient methods for thio-oligosaccharide synthesis is crucial for glycobiology research.

Purpose of the Study:

  • To develop a protecting-group-free strategy for synthesizing thio-oligosaccharides.
  • To utilize highly reactive polymer-bound sugar thiolates in glycosylation reactions.

Main Methods:

  • Reaction of polymer-bound sugar 1-thiolates with sugar triflates.
  • Utilizing highly reactive intermediates without protecting groups.

Main Results:

  • Thio-oligosaccharides were synthesized in high yield.
  • The reaction proceeded efficiently due to the high reactivity of the polymer-bound sugar thiolates.

Conclusions:

  • Protecting-group-free synthesis of thio-oligosaccharides is feasible using polymer-bound sugar thiolates.
  • This approach offers a high-yielding and potentially streamlined route to complex carbohydrates.