Jump to main content
Jump to site search

Issue 12, 2017
Previous Article Next Article

Total synthesis of phenylpropanoid glycoside osmanthuside-B6 facilitated by double isomerisation of glucose–rhamnose orthoesters

Author affiliations

Abstract

A convenient synthesis of phenylpropanoid glycoside osmanthuside-B6 is disclosed. The key steps involved regioselective coumaroylation and rhamnosylation of unprotected phenylethyl-β-D-glucopyranoside to give 2- and 3-O-rhamnosyl orthoester glucopyranosides. Rearrangement of these orthoesters followed by selective removal of their acetyl and allyl groups gave osmanthuside-B6 in 22% overall yield. The rearrangement involved a newly discovered glucose–rhamnose orthoester double isomerization process that has the potential to provide a convenient access to many complex phenylpropanoid glycosides. The synthetic route developed is envisioned to serve as a model for the preparation of phenylpropanoid glucosides having a (substituted) cinnamoyl moiety at O-6 and a saccharide moiety at O-3.

Graphical abstract: Total synthesis of phenylpropanoid glycoside osmanthuside-B6 facilitated by double isomerisation of glucose–rhamnose orthoesters

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 25 Jan 2017, accepted on 01 Mar 2017 and first published on 01 Mar 2017


Article type: Paper
DOI: 10.1039/C7OB00198C
Citation: Org. Biomol. Chem., 2017,15, 2638-2646
  •   Request permissions

    Total synthesis of phenylpropanoid glycoside osmanthuside-B6 facilitated by double isomerisation of glucose–rhamnose orthoesters

    D. T. Khong and Z. M. A. Judeh, Org. Biomol. Chem., 2017, 15, 2638
    DOI: 10.1039/C7OB00198C

Search articles by author