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

Carbohydrate Research
Filip S EkholmReko Leino

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.

References

Aug 5, 2003·Phytochemistry·Tripetch KanchanapoomKazuo Yamasaki
Oct 2, 2007·Phytochemistry·Changhong HuoQingying Zhang

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Citations

Aug 28, 2015·Journal of Agricultural and Food Chemistry·Ya-Nan YangPei-Cheng Zhang
Sep 21, 2012·Organic & Biomolecular Chemistry·Jenny BarbierAndreas Kirschning

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