Hydroxyethylphosphonic acid

Imai. S., Seto, H., Ogawa, H., Satoh, A., and Otake, N., Studies on the biosynthesis of fosfomycin. Conversion of 2-hydroxyethylphosphonic acid and 2-aminoethylphosphonic acid to fosfomycin, Agric. Biol. Chem., 49, 873. 1985. 

Sumitomo Chemical Co., Ltd., a-Hydroxyethylphosphonic Acid, Japanese Patent 60 89,491, 1985. 

The first synthesis of an ot-halogenophosphonic acid by nucleophilic halogenation, described in 1922, involved treating a-phenyl-a-hydroxyethylphosphonic acid with concentrated HCl. It gave a-phenyl-a-chloroethylphosphonic acid in 96% yield. ... 

Kinetic resolution of ( ) diethyl 1,2-epoxyethylphosphonate has been achieved by stirring the epoxide in the presence of catalytic quantities of (R,/ )-A/,A -b (3,5-di-Zert-butylsalicylidene)-l,2-cyclohexanediaminocobaltdll) acetate and HjO at 20°C for 4 days. The reaction mixture becomes very viscous within the first few hours, consistent with the rapid conversion of some of the epoxide into the corresponding diol. After 4 days, the unreacted epoxide is isolated by flash chromatography (39%). It consists essentially of a single enantiomer. The (7 )-conflguration of the resolved epoxide has been established by conversion into the natural product (7 )-2-amino-l-hydroxyethylphosphonic acid (Scheme 4.44). °... 

Hammerschmidt, E, Biosynthesis of natural substances with a P-C bond. Part 11. Incorporation of L-lmethyl- Hjlmethionine and 2-[hydroxy- O]hydroxyethylphosphonic acid in phosphomycin in Streptomyces fradiae - an unusual methyl transfer. Angew. Chem., Int. Ed. Engl., 33, 341, 1994. 

Trichloro-l-hydroxyethylphosphonic acid dimethyl ester, see Trichlorfon Trichlorometafos, see Ronnel... 

Trichlorfon [2,2,2-Trichloro-1 -hydroxyethylphosphonic acid, dimethyl ester] C4H,Cl30/ 62-68-6 1 mg/m ... 

Hammerschmidt P (1994) Incorporation of L-[methyl- H3]methionine and 2-[hydroxy- 0] hydroxyethylphosphonic acid into fosfomydn in Streptomyces fradiae-An unusual methyl-transfer. Angew Chem Int Ed Engl 33 341-342... 

Wyatt PB, Blakskjeer P. An enantioselective synthesis of (R)-2-amino-l-hydroxyethylphosphonic acid by hydrolytic kinetic resolution of ( )-diethyl oxiranephosphonate. Tetrahedron Lett. 1999 40 6481 83. 

Hammerschmidt F, Lindner W, Wuggenig F, Zarbl E. Enzymes in organic chemistry. Part 10. Chemo-enzymatic synthesis of L-phosphaserine and L-phosphaisoserine and enantioseparation of amino-hydroxyethylphosphonic acids by non-aqueous capdlary electrophoresis with quinine carbamate as chiral ion pair agent. Tetrahedron Asymm. 2000 11 2955-2964. 

However, it has been reported, and proved by mass spectrometry, that diethyl 1-methyl-1,2-epoxyethylphosphonate is attacked at the a-position by alcohols under acid-catalysis conditions (BF3Et2O or H2SO4) to give diethyl 1-alkoxy-l-methyl-2-hydroxyethylphosphonates. ... 

Hydroxy-2,2,2-trichloroethylphosphonic acid dimethyl ester (2,2,2-Trichloro-1-hydroxyethyl) dimethylphosphonate 2,2,2-Trichloro-1-hydroxyethylphosphonate, dimethyl ester (2,2,2-Thchloro-l-hydroxyethyl) phosphonic acid dimethyl ester Trichlorophon Trichlorphene Trichlorphon Empirical C4H8CI3O4P Formula (CH30)2P(0)CH(OH)CCl3 Properties Wh. cryst. solid sol. in water, alcohols, ketones, benzene, chloroform, ether si. sol. in aromatic soivs., petrol, ether insol. in oils m.w. 257.45 dens. 1.73 (20/4 C) m.p. 83-84 C b.p. 

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