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

Filip S. Ekholm; Patrik Christoffer Eklund; Reko Leino

doi:10.1016/j.carres.2010.06.008

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

Filip S. Ekholm, Patrik Christoffer Eklund, Reko Leino

Research output: Contribution to journal › Article › Scientific › peer-review

9 Citations (Scopus)

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 language	Undefined/Unknown
Pages (from-to)	1963–1967
Number of pages	5
Journal	Carbohydrate Research
Volume	345
Issue number	13
DOIs	https://doi.org/10.1016/j.carres.2010.06.008
Publication status	Published - 2010
MoE publication type	A1 Journal article-refereed

Keywords

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

Access to Document

10.1016/j.carres.2010.06.008

Cite this

@article{b7bf9e87048c431bad3848cdec1446df,

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

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.",

keywords = "Lignan glycoside, NMR spectroscopy, Semi-synthesis, Trachelospermum asiaticum var. intermedium, Lignan glycoside, NMR spectroscopy, Semi-synthesis, Trachelospermum asiaticum var. intermedium, Lignan glycoside, NMR spectroscopy, Semi-synthesis, Trachelospermum asiaticum var. intermedium",

author = "Ekholm, \{Filip S.\} and Eklund, \{Patrik Christoffer\} and Reko Leino",

year = "2010",

doi = "10.1016/j.carres.2010.06.008",

language = "Odefinierat/ok{\"a}nt",

volume = "345",

pages = "1963–1967",

journal = "Carbohydrate Research",

issn = "0008-6215",

publisher = "Elsevier",

number = "13",

}

TY - JOUR

T1 - A short semi-synthesis and complete NMR-spectroscopic characterization of the naturally occurring lignan glycoside matairesinol 4,4 '-di-O-beta-D-diglucoside

AU - Ekholm, Filip S.

AU - Eklund, Patrik Christoffer

AU - Leino, Reko

PY - 2010

Y1 - 2010

N2 - 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.

AB - 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.

KW - Lignan glycoside

KW - NMR spectroscopy

KW - Semi-synthesis

KW - Trachelospermum asiaticum var. intermedium

KW - Lignan glycoside

KW - NMR spectroscopy

KW - Semi-synthesis

KW - Trachelospermum asiaticum var. intermedium

KW - Lignan glycoside

KW - NMR spectroscopy

KW - Semi-synthesis

KW - Trachelospermum asiaticum var. intermedium

U2 - 10.1016/j.carres.2010.06.008

DO - 10.1016/j.carres.2010.06.008

M3 - Artikel

SN - 0008-6215

VL - 345

SP - 1963

EP - 1967

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 13

ER -