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Journal ArticleDOI

RuCl2(PPh3)3-catalyzed transfer hydrogenation of d-glucose

15 Sep 1992-Journal of Molecular Catalysis (Elsevier)-Vol. 75, Iss: 2, pp 199-208
TL;DR: In this paper, a mixed solvent system such as dimethylacetamide-water and dioxane-water is used for the transfer hydrogenation of glucose to a mixture of mixed solvent systems.
About: This article is published in Journal of Molecular Catalysis.The article was published on 1992-09-15. It has received 16 citations till now. The article focuses on the topics: Benzyl alcohol & Cyclohexanol.
Citations
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Journal ArticleDOI
TL;DR: A review of the recent developments in liquid phase chemical conversions of monosaccharides, disaccharide, and polysaccharides can be found in this paper, followed by a process-driven approach where the existing carbohydrate conversion pathways are classified according to the types of chemical processes involved.

271 citations

Journal ArticleDOI
TL;DR: In this article, the authors provide an overview of the most important recent developments in homogeneous catalysis towards the production and transformation of biomass and biomass related model compounds, including the chemical valorisation of the main components of lignocellulosic biomass.

244 citations

Journal ArticleDOI
TL;DR: In this paper, the TCSM (tethered complex on supported metal) catalysts were used to catalyze the hydrogenation of arenes (Rh−CNR2/Pd−SiO2 and rhCl[CN(CH2)3Si(OC2H5)3]2) under mild conditions of 40 °C and 1 atm.

59 citations

Journal ArticleDOI
07 May 2013-PLOS ONE
TL;DR: To the authors' knowledge, this is the first asymmetric aldol condensation process achieved with whole-cell DERA catalysis and it simplifies and extends previously developed DERA-catalyzed approaches based on the isolated enzyme.
Abstract: Employing DERA (2-deoxyribose-5-phosphate aldolase), we developed the first whole-cell biotransformation process for production of chiral lactol intermediates useful for synthesis of optically pure super-statins such as rosuvastatin and pitavastatin. Herein, we report the development of a fed-batch, high-density fermentation with Escherichia coli BL21 (DE3) overexpressing the native E. coli deoC gene. High activity of this biomass allows direct utilization of the fermentation broth as a whole-cell DERA biocatalyst. We further show a highly productive bioconversion processes with this biocatalyst for conversion of 2-substituted acetaldehydes to the corresponding lactols. The process is evaluated in detail for conversion of acetyloxy-acetaldehyde with the first insight into the dynamics of reaction intermediates, side products and enzyme activity, allowing optimization of the feeding strategy of the aldehyde substrates for improved productivities, yields and purities. The resulting process for production of ((2S,4R)-4,6-dihydroxytetrahydro-2H-pyran-2-yl)methyl acetate (acetyloxymethylene-lactol) has a volumetric productivity exceeding 40 g L−1 h−1 (up to 50 g L−1 h−1) with >80% yield and >80% chromatographic purity with titers reaching 100 g L−1. Stereochemical selectivity of DERA allows excellent enantiomeric purities (ee >99.9%), which were demonstrated on downstream advanced intermediates. The presented process is highly cost effective and environmentally friendly. To our knowledge, this is the first asymmetric aldol condensation process achieved with whole-cell DERA catalysis and it simplifies and extends previously developed DERA-catalyzed approaches based on the isolated enzyme. Finally, applicability of the presented process is demonstrated by efficient preparation of a key lactol precursor, which fits directly into the lactone pathway to optically pure super-statins.

39 citations

Journal ArticleDOI
TL;DR: In this article, the authors show that the treatment of partially protected or unprotected carbohydrates with the RhH(PPh 3 ) 4 -benzalacetone system leads exclusively to glycono-1,4-lactones by regioselective oxidation and subsequent ring restriction.

39 citations

References
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Journal ArticleDOI
TL;DR: In this paper, the rate of D-glucose disproportionation in tetrahydrofurfuryl alcohol (THFA) catalysed by RuHCl(CO)(PPh3)3 is suggested.

8 citations