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Synthesis of Dense and Chiral Dendritic Polyols Using Glyconanosynthon Scaffolds.

  • Shiao TC Pharmaqam and Nanoqam, Department of Chemistry, University of Québec a Montréal, P.O. Box 8888, Succ. Centre-Ville, Montréal, QC H3C 3P8, Canada. chichi_shiao@hotmail.com.
  • Rej R Pharmaqam and Nanoqam, Department of Chemistry, University of Québec a Montréal, P.O. Box 8888, Succ. Centre-Ville, Montréal, QC H3C 3P8, Canada. rabi.rej@hotmail.com.
  • Rose M Pharmaqam and Nanoqam, Department of Chemistry, University of Québec a Montréal, P.O. Box 8888, Succ. Centre-Ville, Montréal, QC H3C 3P8, Canada. mariecka.rose@hotmail.fr.
  • Pavan GM Department of Innovative Technologies, University of Applied Sciences and Arts of Southern Switzerland, Galleria 2, Manno CH-6928, Switzerland. giovanni.pavan@supsi.ch.
  • Roy R Pharmaqam and Nanoqam, Department of Chemistry, University of Québec a Montréal, P.O. Box 8888, Succ. Centre-Ville, Montréal, QC H3C 3P8, Canada. roy.rene@uqam.ca.
  • 2016-04-07
Published in:
  • Molecules (Basel, Switzerland). - 2016
CuAAAC
carbohydrate
click chemistry
dendrimer
glycodendrimer
thiol-ene
thiol-yne
Alcohols
Click Chemistry
Dendrimers
Molecular Structure
Polymers
Sulfhydryl Compounds
Surface Properties
English Most classical dendrimers are frequently built-up from identical repeating units of low valency (usually AB2 monomers). This strategy necessitates several generations to achieve a large number of surface functionalities. In addition, these typical monomers are achiral. We propose herein the use of sugar derivatives consisting of several and varied functionalities with their own individual intrinsic chirality as both scaffolds/core as well as repeating units. This approach allows the construction of chiral, dense dendrimers with a large number of surface groups at low dendrimer generations. Perpropargylated β-D-glucopyranoside, serving as an A5 core, together with various derivatives, such as 2-azidoethyl tetra-O-allyl-β-D-glucopyranoside, serving as an AB4 repeating moiety, were utilized to construct chiral dendrimers using "click chemistry" (CuAAC reaction). These were further modified by thiol-ene and thiol-yne click reactions with alcohols to provide dendritic polyols. Molecular dynamic simulation supported the assumption that the resulting polyols have a dense structure.
Language
  • English
Open access status
gold
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Persistent URL
https://sonar.ch/global/documents/279037
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