A short semi-synthesis and complete NMR-spectroscopic characterization of the naturally occurring lignan glycoside matairesinol 4,4 '-di-O-beta-D-diglucoside

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    Abstract

    A convenient semi-synthesis of (8R,8'R)-matairesinol 4,4'-di-O-beta-D-glucopyranoside (MDG), found in the stems of Trachelospermum asiaticum var. intermedium, is described starting from the readily available starting materials D-glucose and hydroxymatairesinol. By this approach the synthesis of MDG can be accomplished in six steps with an overall yield of 28%. In addition, the first complete NMR-spectroscopic characterization of MDG was accomplished by the combination of standard NMR techniques and spectral simulations performed with the PERCH NMR simulation software. (C) 2010 Elsevier Ltd. All rights reserved.
    Original languageUndefined/Unknown
    Pages (from-to)1963–1967
    Number of pages5
    JournalCarbohydrate Research
    Volume345
    Issue number13
    DOIs
    Publication statusPublished - 2010
    MoE publication typeA1 Journal article-refereed

    Keywords

    • Lignan glycoside
    • NMR spectroscopy
    • Semi-synthesis
    • Trachelospermum asiaticum var. intermedium

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