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Issue 12, 2017
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Total synthesis of phenylpropanoid glycoside osmanthuside-B6 facilitated by double isomerisation of glucose–rhamnose orthoesters

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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

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Supplementary files

Article information


Submitted
25 Jan 2017
Accepted
01 Mar 2017
First published
01 Mar 2017

Org. Biomol. Chem., 2017,15, 2638-2646
Article type
Paper

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

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