40962-37-6

Usage

InChI:InChI=1/C3H7O5P/c1-8-3(4)2-9(5,6)7/h2H2,1H3,(H2,5,6,7)

Upstream product

• 67-56-1 methanol 
• 65868-40-8 ethyl P,P-bis(trimethylsilyl) phosphonoacetate 
• 4408-78-0 phosphonoacetic acid 
• 485-80-3 S-adenosyl-L-methionine 
• 5927-18-4 trimethyl phosphonoacetate 
• 1067-74-9 Methyl diethylphosphonoacetate 
• 67605-34-9 methyl 2-(bis((trimethylsilyl)oxy)phosphoryl)acetate 

Downstream Products

• 143140-39-0 methyl 2-cyclobutylideneacetate 
• 88738-78-7 bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate 
• 1280206-23-6 (E)-3-[5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-acrylic acid methyl ester 
• 870092-45-8 methyl 2-(4-(dimethylamino)-4-phenylcyclohexylidene)acetate 

Relevant academic research and scientific papers

Biosynthesis of fosfazinomycin is a convergent process

Fosfazinomycin A is a phosphonate natural product in which the C-terminal carboxylate of a Val-Arg dipeptide is connected to methyl 2-hydroxy-2-phosphono-acetate (Me-HPnA) via a unique hydrazide linkage. We report here that Me-HPnA is generated from phosphonoacetaldehyde (PnAA) in three biosynthetic steps through the combined action of an O-methyltransferase (FzmB) and an α-ketoglutarate (α-KG) dependent non-heme iron dioxygenase (FzmG). Unexpectedly, the latter enzyme is involved in two different steps, oxidation of the PnAA to phosphonoacetic acid as well as hydroxylation of methyl 2-phosphonoacetate. The N-methyltransferase (FzmH) was able to methylate Arg-NHNH2 (3) to give Arg-NHNHMe (4), constituting the second segment of the fosfazinomycin molecule. Methylation of other putative intermediates such as desmethyl fosfazinomycin B was not observed. Collectively, our current data support a convergent biosynthetic pathway to fosfazinomycin.

The mckenna reaction – avoiding side reactions in phosphonate deprotection

The McKenna reaction is a well-known and popular method for the efficient and mild synthesis of organophosphorus acids. Bromotrimethylsilane (BTMS) is the main reagent in this reaction, which transforms dialkyl phosphonate esters into bis(trimethylsilyl)esters, which are then easily converted into the target acids. However, the versatile character of the McKenna reaction is not always used to its full extent, due to formation of side products. Herein, demonstrated by using model examples we have not only analyzed the typical side processes accompanying the McKenna reaction, but also uncovered new ones. Further, we discovered that some commonly recommended precautions did not always circumvent the side reactions. The proposed results and recommendations may facilitate the synthesis of phosphonic acids.

Facile Two-Step Synthesis of Methyl Bis(2,2,2-trifluoroethyl)phosphonoacetate by Exploiting Garegg-Samuelsson Reaction Conditions

A facile two-step synthesis of methyl bis(2,2,2-trifluoroethyl)phosphonoacetate (Still-Gennari reagent) has been developed by exploiting Garegg-Samuelsson reaction conditions. Starting from trimethyl phosphonoacetate, Still-Gennari reagent was prepared in 94% yield via methyl 2-{bis[(trimethylsilyl)oxy]phosphoryl}acetate intermediate. This synthetic procedure was also used to prepare some kinds of Horner-Wadsworth-Emmons reagents and related compounds.

Use of a phosphonate methyltransferase in the identification of the fosfazinomycin biosynthetic gene cluster

Natural product discovery has been boosted by genome mining approaches, but compound purification is often still challenging. We report an enzymatic strategy for stable isotope labeling of phosphonates in extract (SILPE) that facilitates their purificatio

Dealkylation of phosphonate esters with chlorotrimethylsilane

Chlorotrimethylsilane completely dealkylates phosphonate esters at elevated temperature in a sealed reaction vessel. These conditions are tolerated by a variety of functional groups and lead to high conversions of dimethyl, diethyl and diisopropyl phosphonates to their corresponding phosphonic acids.

Intramolecular cyclopropanation reactions en route to novel P- heterocycles

The first examples of intramolecular cyclopropanation reactions on a phosphonate template catalyzed by Rh2(OAc)4 are described. These reactions proceed in excellent yield and give mixtures of the P-heterocycles cis-2a-d and trans-2a-d with moderate levels of diastereoselectivity. The diastereoselectivity of this transformation is dependent upon the size of the alkyl group R contained in the alkyl α-diazodiallylphosphonoacetate starting materials 1a-d.

Treatment of herpes simplex infections

A method of treating herpes simplex infections in warm-blooded animals by administering to said animals a carboxylic ester of phosphonoacetic acid of the formula STR1 wherein R is a C1 -C2 alkyl.