Synthesis and fundamental HSQC NMR data of monolignol β-glycosides, dihydromonolignol β-glycosides and p-hydroxybenzaldehyde derivative β-glycosides for the analysis of phenyl glycoside type lignin-carbohydrate complexes (LCCs)
Abstract
Twelve monolignol (coniferyl alcohol, sinapyl alcohol and p-coumaryl alcohol) β-glycosides (β-glucosides, β-galactosides, β-xylosides and β-mannosides) were synthesised to obtain fundamental NMR data for the analysis of phenyl glycoside type lignin-carbohydrate complexes (LCCs). That is, the 1,2-trans glycosides (the β-glucosides, β-galactosides and β-xylosides) and the 1,2-cis glycosides (the β-mannosides) were synthesized by means of Koenig-Knorr glycosylation and β-selective Mitsunobu glycosylation strategies, respectively. In addition, dihydromonolignol and p-hydroxybenzaldehyde derivative β-glycosides were also prepared from the corresponding monolignol glycosides and their intermediates, respectively. The correlation observed for the C1β-H1β bonds of the sugar moieties in the HSQC spectra of the all β-glycosides varied and were in the range of δC/δH 96–104/4.7–5.4 ppm. Especially, it was found that the correlations derived from the C1β-H1β bonds of the guaiacyl and p-hydroxyphenyl β-mannosides were close to those derived from the C1α-H1α bonds of the 4-O-methyl-α-D-glucuronic acid moieties described in the literature.
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©2014 by De Gruyter
Articles in the same Issue
- Frontmatter
- Original Articles
- Modeling of alkaline extraction chemistry and kinetics of softwood kraft pulp
- Synthesis and fundamental HSQC NMR data of monolignol β-glycosides, dihydromonolignol β-glycosides and p-hydroxybenzaldehyde derivative β-glycosides for the analysis of phenyl glycoside type lignin-carbohydrate complexes (LCCs)
- Iridoids from the stems of Viburnum erosum
- 6-Pentyl-α-pyrone as an anti-sapstain compound produced by Trichoderma gamsii KUC1747 inhibits the germination of ophiostomatoid fungi
- ESR studies on the free radical generation in wood by irradiation with selected sources from UV to IR wavelength regions
- Synthesis of aluminum hydroxide thin coating and its influence on the thermomechanical and fire-resistant properties of wood
- Lignin distribution in waterlogged archaeological Picea abies (L.) Karst degraded by erosion bacteria
- Assessment of covalent bond formation between coupling agents and wood by FTIR spectroscopy and pull strength tests
- Effect of hot water extracted hardwood and softwood chips on particleboard properties
- The interrelation between microfibril angle (MFA) and hygrothermal recovery (HTR) in compression wood and normal wood of Sugi and Agathis
- Chemical remediation of wood treated with micronised, nano or soluble copper preservatives
- Energetic investigation of the fatigue of wood
- Chemical and ultrastructural changes in compound middle lamella (CML) regions of softwoods thermally modified by the Termovuoto process
- Short Note
- Properties of young Araucaria heterophylla (Norfolk Island pine) reaction and normal wood
- Effect of specimen configuration on the measurement of off-axis logarithmic decrement of solid wood measured by longitudinal and flexural vibration tests
Articles in the same Issue
- Frontmatter
- Original Articles
- Modeling of alkaline extraction chemistry and kinetics of softwood kraft pulp
- Synthesis and fundamental HSQC NMR data of monolignol β-glycosides, dihydromonolignol β-glycosides and p-hydroxybenzaldehyde derivative β-glycosides for the analysis of phenyl glycoside type lignin-carbohydrate complexes (LCCs)
- Iridoids from the stems of Viburnum erosum
- 6-Pentyl-α-pyrone as an anti-sapstain compound produced by Trichoderma gamsii KUC1747 inhibits the germination of ophiostomatoid fungi
- ESR studies on the free radical generation in wood by irradiation with selected sources from UV to IR wavelength regions
- Synthesis of aluminum hydroxide thin coating and its influence on the thermomechanical and fire-resistant properties of wood
- Lignin distribution in waterlogged archaeological Picea abies (L.) Karst degraded by erosion bacteria
- Assessment of covalent bond formation between coupling agents and wood by FTIR spectroscopy and pull strength tests
- Effect of hot water extracted hardwood and softwood chips on particleboard properties
- The interrelation between microfibril angle (MFA) and hygrothermal recovery (HTR) in compression wood and normal wood of Sugi and Agathis
- Chemical remediation of wood treated with micronised, nano or soluble copper preservatives
- Energetic investigation of the fatigue of wood
- Chemical and ultrastructural changes in compound middle lamella (CML) regions of softwoods thermally modified by the Termovuoto process
- Short Note
- Properties of young Araucaria heterophylla (Norfolk Island pine) reaction and normal wood
- Effect of specimen configuration on the measurement of off-axis logarithmic decrement of solid wood measured by longitudinal and flexural vibration tests