Microwave-Assisted Protocols Applied to the Synthesis of 1′,2,3,3′,4,4′-Hexa-O-benzylsucrose

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Abstract

The sucrose derivative 1′,2,3,3′,4,4′-hexa-O-benzylsucrose is a key intermediate for the chemoselective synthesis of various useful materials, such as macrocycles, crown ether analogs, and polymers. Several strategies for the synthesis of this compound were explored by applying microwave-assisted protocols, thus permitting significant reductions of time and energy compared to other routes. The outcomes of the different approaches were compared and the optimal one, in terms of yield and reproducibility, was found to be the initial protection at the positions 6 and 6′, withtert-butyldiphenylsilylchloride (TBDPSCl) in the presence of 4-(dimethylamino)pyridine (4-DMAP) and pyridine as a solvent, then perbenzylation of the remaining hydroxyl groups, followed by selective deprotection of the TBDPS groups to obtain the title compound.
Original languageEnglish
Pages (from-to)3027-3036
JournalSynthetic Communications
Volume44
Issue number20
DOIs
Publication statusPublished - 2014

Keywords

  • Carbohydrates
  • chemoselective synthesis
  • microwave chemistry
  • protection-deprotection strategies
  • sucrose derivatives

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