Synthetic and spectroscopic studies of 2-C-methyl-erythritol and 2-C-methyl-threito

Anthonsen, T.; Hagen, Steinar; Sallam, Mohammed A.E.

doi:10.1016/s0031-9422(00)91030-6

Cited by 25 publications

(21 citation statements)

References 10 publications

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“…2‐ C ‐Methyl‐ D‐ erythritol (7 mg) was dissolved in 9 ml of dry acetone. Dichloromethane (2 ml) containing 1 M ZnCl 2 ·Et 2 O were added in one portion at room temperature [19]. After 5 h, 50 ml of chloroform was added and the solution was washed three times with 10 ml of 5% NaHCO 3 (w/v) and subsequently with 10 ml of water.…”

Section: Methodsmentioning

confidence: 99%

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Biosynthesis of terpenoids: 1‐deoxy‐D‐xylulose‐5‐phosphate reductoisomerase from Escherichia coli is a class B dehydrogenase

et al. 2000

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Section: Methodsmentioning

confidence: 99%

“…2). [19]. After 5 h, 50 ml of chloroform was added and the solution was washed three times with 10 ml of 5% NaHCO 3 (w/v) and subsequently with 10 ml of water.…”

Section: Preparation Of (4s)-[4-2 H 1 ]Nadph [17]mentioning

confidence: 99%

Biosynthesis of terpenoids: 1‐deoxy‐D‐xylulose‐5‐phosphate reductoisomerase from Escherichia coli is a class B dehydrogenase

et al. 2000

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“…We decided 25 to use the strategy of Moen et al (Moen et al, 2007) because it requires the least number of steps. It takes up the procedures described by Anthonsen et al (Anthonsen et al, 1976(Anthonsen et al, , 1980 for the preparation of the two diastereomeric tetraols as racemates.…”

Section: Aqueous Tetraol Samplesmentioning

confidence: 99%

“…Our solution to this problem was to convert the tetraols into the diacetonides 5 in order to mask the highly polar hydroxyl groups and therefore allow standard column chromatography on silica gel to be applied 15 for the removal of the inorganic salts as well as organic side products. The synthesis of the diacetonide (2S,3R) 100 -5 has been described (Anthonsen et al, 1980;Proteau et al, 1999). Just as Proteau et al (Proteau et al, 1999) we used 2,2-dimethoxypropane in the presence of toluene sulfonic acid.…”

Section: In Order To Obtain Enantiomerically Enriched Materials Kinementioning

confidence: 99%

“…One-step esterifications of the diacids (Z)-and (E)-1 on a scale of up to 100 g were achieved with ethanol and sulfuric acid as the reagents (Anthonsen et al, 1980;Kar and Argade, 2002;Klimovica et al, 2011;Tripp et al, 2005) the reaction mixture to reflux in a Soxhlet extractor with a thimble filled with MgSO 4 for trapping the evolving water. The diesters (Z)-and (E)-2 were isolated by washing with base and subsequent distillation.…”

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Physical state of 2-methylbutane-1,2,3,4-tetraol in pure and internally mixed aerosols

Lessmeier¹,

Dette²,

Godt³

et al. 2018

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Abstract. 2-Methylbutane-1,2,3,4-tetraol (hereafter named tetraol) is an important oxidation product of isoprene and can be considered as a marker compound for isoprene-derived secondary organic aerosols (SOAs). Little is known about this compound's physical phase state, although some field observations indicate that isoprene-derived secondary organic aerosols 10 in the tropics tend to be in a liquid rather than a solid state. To gain more knowledge about the possible phase states of tetraol and of tetraol-containing SOA particles, we synthesized tetraol as racemates as well as enantiomerically enriched materials.Subsequently the obtained highly viscous dry liquids were investigated calorimetrically by differential scanning calorimetry revealing subambient glass transitions temperatures . We also show that only the diastereomeric isomers differ in their values, albeit only by a few kelvin. We derive the phase diagram of water/tetraol mixtures over the whole tropospheric 15 temperature and humidity range from determining glass transition temperatures and ice melting temperatures of aqueous tetraol mixtures. We also investigated how water diffuses into a sample of dry tetraol. We show that upon water uptake two homogeneous liquid domains form that are separated by a sharp, locally constrained concentration gradient. Finally, we measured the glass transition temperatures of mixtures of tetraol and an important oxidation product of α-pinene-derived SOA:3-methylbutane-1,2,3-tricaboxylic acid (3-MBTCA). Overall, our results imply a liquid-like state of isoprene-derived SOA 20 particle in the lower troposphere at moderate to high relative humidity, but presumably a semisolid or even glassy state at upper tropospheric conditions, particularly at low relative humidity, thus providing experimental support for recent modelling calculations. 30Atmos. Chem. Phys. Discuss., https://doi

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Chemo‐Enzymatic Synthesis of All Isomers of 2‐Methylbutane‐1,2,3,4‐tetraol – Important Contributors to Atmospheric Aerosols

2007

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By a combination of stereospecific osmium catalyzed oxidation of dimethyl citraconate and lipase catalysed enantioselective resolution of the formed dimethyl (2R*,3S*)‐2,3‐dihydroxy‐2‐methylbutanedioate, followed by reduction, (2R,3S)‐ and (2S,3R)‐2‐methylbutane‐1,2,3,4‐tetraol were isolated. Similar reactions starting with dimethyl mesaconate gave the isomers, (2R,3R)‐ and (2S,3S)‐2‐methylbutane‐1,2,3,4‐tetraol. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Synthetic and spectroscopic studies of 2-C-methyl-erythritol and 2-C-methyl-threito

Cited by 25 publications

References 10 publications

Biosynthesis of terpenoids: 1‐deoxy‐D‐xylulose‐5‐phosphate reductoisomerase from Escherichia coli is a class B dehydrogenase

Biosynthesis of terpenoids: 1‐deoxy‐D‐xylulose‐5‐phosphate reductoisomerase from Escherichia coli is a class B dehydrogenase

Physical state of 2-methylbutane-1,2,3,4-tetraol in pure and internally mixed aerosols

Chemo‐Enzymatic Synthesis of All Isomers of 2‐Methylbutane‐1,2,3,4‐tetraol – Important Contributors to Atmospheric Aerosols

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