L-(S)-Erythrulose: The synthesis of (R)-1,2,4-butanetriol and of some related C4 chirons.

Eycken, Erik V. Van der; Wilde, H. De; Deprez, L.; Vandewalle, M.

doi:10.1016/s0040-4039(00)96619-x

Cited by 24 publications

(8 citation statements)

References 12 publications

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“…Most notably, the 62R conguration was reconrmed based on the positive specic rotation ([a] 25 D ¼ + 8 (c ¼ 0.02, methanol)) of fragment 1d (Fig. 2), 28,29 whereas the 66S conguration was further supported by the positive Dd SR sign values of H 2 -65 and methyl protons of the terminal pivaloyl ester in 1e (Fig. 5).…”

Section: Absolute Conguration and Bioactivities Of Benthol Amentioning

confidence: 95%

Discovery of benthol A and its challenging stereochemical assignment: opening up a new window for skeletal diversity of super-carbon-chain compounds

Jiang

Sun

et al. 2021

Chem. Sci.

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Section: Absolute Conguration and Bioactivities Of Benthol Amentioning

confidence: 95%

Discovery of benthol A and its challenging stereochemical assignment: opening up a new window for skeletal diversity of super-carbon-chain compounds

Jiang

Sun

et al. 2021

Chem. Sci.

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“…The potential of this new chiral building block for the synthesis of biologically active compounds, such as GABOB, Biotin, Swainsonin, etc. has been explored in depth at Gent University by the group of Prof. Vandewalle [27,28].…”

Section: Pharmaceuticals (Fig 14)mentioning

confidence: 99%

Erythritol, a New Raw Material for Food and Non‐food Applications

Röper¹,

Goossens²

1993

Starch Stärke

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In response to an increasing demand from consumers for healthier and calorie controlled foods, Cerestar has developed a new food ingredient, erythritol. Erythritol can be produced from starch by a full biotechnological process, combining enzymatic and fermentative conversions. The use of an osmophilic yeast allows the fermentation step to be performed at high dry substance, giving an economic advantage. An extremely pure end product is then easily obtained by final crystallisation. Erythritol is structurally a polyol and shares the health properties of other polyols such as being toothfriendly and safe for diabetics. However, it offers in addition two very important nutritional advantages: a lower calorific value (0.3 Kcal/g) and a good tolerance. This is due to its low molecular weight, which allows erythritol to be rapidly absorbed from the small intestine, with subsequent excretion in the urine. Fermentation in the colon is therefore excluded and any resulting gastro‐intestinal discomfort avoided. The combination of these properties makes erythritol a unique low calorie bulk sweetener. From a functionality point of view, erythritol is a moderately sweet bulking agent with a cooling taste: workability is similar to other polyols. It has a taste profile close to that of sucrose and may therefore improve the taste quality of a blend with intense sweeteners. Its low solubility and ease of crystallisation, make erythritol very suitable for applications which require a crystalline sweetener, such as chocolate. Other potential application areas are bakery, table‐top and confectionery. Presently erythritol is under evaluation to establish beyond any doubt its safety and to obtain food approval as a new, low calorie, bulk sweetener. Potential non‐food applications of erythritol are in polymers, fine chemicals and pharmaceutical intermediates.

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“…The optically active chiral L-erythrulose is structurally related to the formerly mentioned non chiral meso-erythritol. This interesting compound can be transformed into (R)-l,2,4-butanetriol [51] (Fig. 26) which itself could be an alternative intermediate e. g. for the synthesis of the antiepileptic drug (-)yamino-(R)-P-hydroxybutync acid (GABOB), (D)-biotin or the a-mannosidase inhibitor Swainsonine.…”

Section: Active Materialsmentioning

confidence: 99%

New Industrial Products from Starch

Koch¹,

Röper²

1988

Starch Stärke

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The industrial (non-food) use of starch and starch-based products as renewable raw materials is discussed together with examples, in the following application areas: -Starch as auxiliary raw material: binder, adhesive, thickener, protective colloid. -Starch as raw material for new products in chemical or biotechnical processes: polyols, acids, polysaccharides, enzymes. -Starch as filler with specific functionality for synthetic polymers to improve application properties in e. g. polyethylene, polypropylene, polystyrene, polyurethane-foams, styreneibutadiene copolymers, polyvinylchloride. -Starch as reactive component to be incorporated during production of synthetic polymers leading to synergistic effects: urea/ formaldehyde resins, phenolic resins, alkyd-and melamine resins. -Starch-based active materials which either exhibit direct functionality themselves, (e. g. as surfactants, sequestrants and bleaching boosters) or which represent building blocks for the synthesis of chiral compounds for the pharmaceutical or the agro-industries. Neue lndustrieprodukte aus Starke. Die industrielle Nutzung des nachwachsenden Rohstoffs Starke und Starke basierender Produkte im Non-food-Bereich wird mit Beispielen unter folgenden Gesichtspunkten dargestellt und diskutiert: -Starke als Hilfsrohstoff: Bindemittel, Kleber, Dickungsmittel, Schutzkolloid. -Starke als Rohstoff fur neue Produkte durch chemische oder biotechnische Prozesse: Polyole, Sauren, Polysaccharide, Enzyme. -Starke als Fullstoff mit funktionellen Eigenschaften in synthetischen Polymeren zur Verbesserung von Polymer-Eigenschaften: Polyethylen, Polypropylen, Polystyrol, Polyurethan-Schaume, Styrolmutadien Copolymere, Polyvinylchlorid. -Starke als reaktive Komponente, verwendet bei der Herstellung synthetischer Polymerer unter Ausbildung synergistischer Effekte: HarnstoffiFormaldehyd-Harze, Phenol-Harze, Alkyd-und Melamin-Harze. -Starke basierende aktive Verbindungen, die selbst direkte Funktionalitat zeigen, z. B. als oberflachenaktive Substanzen, Sequestriermittel und Bleich-Verstarker oder die als Synthese-Bausteine fir chirale Verbindungen in der Pharma-oder Agrar-Industrie genutzt werden konnen. starchlstarke 40 (1988) Nr. 4, S. 121-131 0 VCH Verlagsgesellschaft mbH, D-6940 Weinheim, 1988 0038-9056/88/0404-0121$02.50/0 starchhtiirke 40 (1988) Nr. 4, S . 121-131

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L-(S)-Erythrulose: The synthesis of (R)-1,2,4-butanetriol and of some related C4 chirons.

Cited by 24 publications

References 12 publications

Discovery of benthol A and its challenging stereochemical assignment: opening up a new window for skeletal diversity of super-carbon-chain compounds

Discovery of benthol A and its challenging stereochemical assignment: opening up a new window for skeletal diversity of super-carbon-chain compounds

Erythritol, a New Raw Material for Food and Non‐food Applications

New Industrial Products from Starch

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