Phosphonic Acid Analogs of Carbohydrate Metabolites. IV. Synthesis of DL-Glyceraldehyde-3-phosphonic Acid

1973 ◽  
Vol 51 (1) ◽  
pp. 104-110 ◽  
Author(s):  
Erich Baer ◽  
Ranga Robinson
Keyword(s):  
Phosphoric Acid ◽  
Chemical Synthesis ◽  
Phosphonic Acid ◽  
Methylphosphonic Acid ◽  
Diethyl Ester ◽  
Acid Analog ◽  
Protective Groups ◽  
Carbohydrate Metabolites

A chemical synthesis of DL-glyceraldehyde-3-phosphonic acid, the phosphonic acid analog of DL-glyceraldehyde-3-phosphoric acid, is reported. It was obtained from dimer DL-glyceraldehyde by two procedures differing solely in their protective groups via the following intermediates. Procedure 1: 2,5-diiodomethyl-3,6-dimethoxy-1,4-dioxane → 2,5-bis(methylphosphonic acid diethyl ester)-3,6-dimethoxy-1,4-dioxane → 2,5-bis(methylphosphonic acid)-3,6-dimethoxy-1,4-dioxane → DL-glyceraldehyde-3-phosphonic acid. Procedure 2: 2,5-bis(p-toluenesulfonyloxymethyl)-3,6-dibenzoxy-l,4-dioxane → 2,5-diiodomethyl-3,6-dibenzoxy-l,4-dioxane → 2,5-bis(methylphosphonic acid diethyl ester)-3,6-dibenzoxy-l,4-dioxane → 2,5-bis(methylphosphonicacid)-3,6-dibenzoxy-1,4-dioxane → DL-glyceraldehyde-3-phosphonic acid.

Phosphonic acid analogues of carbohydrate metabolites. I. Synthesis of L- and D-dihydroxypropylphosphonic acid

1969 ◽  
Vol 47 (10) ◽  
pp. 955-960 ◽  
Author(s):  
Erich Baer ◽  
Hemendra Basu
Keyword(s):  
Propylene Glycol ◽  
Phosphonic Acid ◽  
Cold Water ◽  
Condensation Product ◽  
Triethyl Phosphite ◽  
Hot Water ◽  
Diethyl Ester ◽  
Mineral Acids ◽  
Optical Rotations ◽  
Carbohydrate Metabolites

A synthesis of the phosphonic acid analogues of L-α- and D-α-glycerophosphoric acid, viz. L- and D-dihydroxypropylphosphonic acid, is described. The L-dihydroxypropylphosphonic acid was obtained by treating acetone α-iodo-L-propylene glycol with triethyl phosphite at 120–125° for 24 h, hydrolyzing the condensation product acetone L-dihydroxypropylphosphonic acid diethyl ester with 2 N sulfuric acid at 100° for 48 h, and isolating the L-dihydroxypropylphosphonic acid as barium salt. The D-dihydroxypropylphosphonic acid was prepared in the same manner from acetone α-iodo-D-propylene glycol. The barium salts are readily soluble in cold water, much less soluble in hot water, and insoluble in the more common organic solvents. Dihydroxypropylphosphonic acid and α-glycerophosphoric acid can be distinguished from each other by their different behaviors towards hot mineral acids, and by the infrared spectra, n.m.r. spectra, and optical rotations of their barium salts.

Tailored protective groups for surface immobilization of ruthenium dyes

2020 ◽  
Vol 49 (12) ◽  
pp. 3735-3742 ◽  
Author(s):  
Sebastian Amthor ◽  
Hanna Braun ◽  
Julius Gröne ◽  
Djawed Nauroozi ◽  
Timo Jacob ◽  
...  
Keyword(s):  
Phosphonic Acid ◽  
High Stability ◽  
Aqueous Media ◽  
Surface Immobilization ◽  
Silyl Ester ◽  
Protective Groups ◽  
Ruthenium Dyes ◽  
Initial Adsorption

Synthesis of a ruthenium based chromophore with a phosphonic acid silyl-ester is reported, which is immobilized onto a NiO surface showing fast initial adsorption, high stability towards desorption in aqueous media and enhanced DSC performance.

scholarly journals Influence of Wastewater Discharge on the Occurrence of PBTC, HEDP, and Aminophosphonates in Sediment, Suspended Matter, and the Aqueous Phase of Rivers

Water ◽  
2020 ◽  
Vol 12 (3) ◽  
pp. 803
Author(s):  
Eduard Rott ◽  
Oliver Happel ◽  
Dominic Armbruster ◽  
Ralf Minke
Keyword(s):  
Phosphonic Acid ◽  
Suspended Matter ◽  
Total Concentration ◽  
Treatment Plant ◽  
Large River ◽  
Solid Particles ◽  
Methylphosphonic Acid ◽  
Wastewater Discharge ◽  
Adsorption Affinity ◽  
One Year

Sediment, suspended matter (SM), and water of a large river (Neckar; River1) and a small river (Körsch; River2) were analyzed for the phosphonates 2-phosphonobutane-1,2,4-tricarboxylic acid (PBTC), 1-hydroxyethylidene (1,1-diphosphonic acid) (HEDP), aminotris (methylphosphonic acid) (ATMP), ethylenediaminetetra (methylene phosphonic acid) (EDTMP), and diethylenetriaminepenta (methylene phosphonic acid) (DTPMP). Ten samplings were performed at intervals of one to two months during one year, each covering the relevant matrices before and behind the discharge point of a wastewater treatment plant (WWTP). In River1, the total concentration of dissolved phosphonate did not change significantly (2.4–5.8 µg/L before vs. 2.5–6.6 µg/L behind WWTP; p = 0.9360). In River2, it increased significantly from <0.1–1.6 µg/L to 19–39 µg/L (p < 0.0001). Based on the median, the total phosphonate load in River1 sediment increased 1.9-fold (6.7–29.4 mg/kg before vs. 17.8–53.5 mg/kg behind WWTP; p = 0.0033) and in River2 by a factor of eight (1.8–5.0 mg/kg before vs. 18.1–51.4 mg/kg behind WWTP; p < 0.0001). This indicates that phosphonates discharged by WWTPs adsorb onto solid particles and accumulate in the sediment. In the case of River2, the SM load could reach values of 1000–1710 mg/kg behind the WWTP, presumably due to the introduction of insufficiently retained activated sludge particles of >2000 mg/kg phosphonate loads. In general, the nitrogen-free phosphonates PBTC and HEDP were most predominant in both dissolved and adsorbed form, of which HEDP had the highest adsorption affinity.

Synthesis of the Phosphonic Acid Analog of Serine

Synthesis ◽  
1984 ◽  
Vol 1984 (07) ◽  
pp. 577-580 ◽  
Author(s):  
Barbara Lejczak ◽  
Paweł Kafarski ◽  
Mirosław Soroka ◽  
Przemysław Mastalerz
Keyword(s):  
Phosphonic Acid ◽  
Acid Analog
Sign in / Sign up

Export Citation Format

Share Document