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

Tutkimustuotos: Lehtiartikkeli › Artikkeli › Tieteellinen › vertaisarvioitu

9 Sitaatiot (Scopus)

Abstrakti

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.

Alkuperäiskieli	Ei tiedossa
Sivut	1963–1967
Sivumäärä	5
Julkaisu	Carbohydrate Research
Vuosikerta	345
Numero	13
DOI - pysyväislinkit	https://doi.org/10.1016/j.carres.2010.06.008
Tila	Julkaistu - 2010
OKM-julkaisutyyppi	A1 Julkaistu artikkeli, soviteltu

Keywords

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

Pääsy asiakirjaan

10.1016/j.carres.2010.06.008

Viittausmuodot

@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",

}

A short semi-synthesis and complete NMR-spectroscopic characterization of the naturally occurring lignan glycoside matairesinol 4,4 '-di-O-beta-D-diglucoside. / Ekholm, Filip S.; Eklund, Patrik Christoffer ; Leino, Reko.
julkaisussa: Carbohydrate Research, Vuosikerta 345, Nro 13, 2010, s. 1963–1967.

Tutkimustuotos: Lehtiartikkeli › Artikkeli › Tieteellinen › vertaisarvioitu

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 -