78186-91-1

Basic information

• Product Name: DiMethoxyphosphinylhydroxy Acetic Acid Methyl Ester
• Synonyms: DiMethoxyphosphinylhydroxy Acetic Acid Methyl Ester
• CAS NO: 78186-91-1
• Molecular Formula: C₅H₁₁O₆P
• Molecular Weight: 198.111001
• Product Categories: Miscellaneous Reagents, Phosphorylating & Phosphitylating Agents
• Mol File: 78186-91-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 59-61 °C(Solv: ethyl acetate (141-78-6); ethyl ether (60-29-7))
• Boiling Point: 285.8±30.0 °C(Predicted)
• Appearance: /
• Density: 1.326±0.06 g/cm3(Predicted)
• PKA: 10.57±0.20(Predicted)
• CAS DataBase Reference: DiMethoxyphosphinylhydroxy Acetic Acid Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: DiMethoxyphosphinylhydroxy Acetic Acid Methyl Ester(78186-91-1)
• EPA Substance Registry System: DiMethoxyphosphinylhydroxy Acetic Acid Methyl Ester(78186-91-1)

Safety Data

• Hazardous Substances Data: 78186-91-1(Hazardous Substances Data)

Usage

Uses

Dimethoxyphosphinylhydroxy Acetic Acid Methyl Ester is involved in release of iron from the serum iron transport protein, transferrin.

Upstream product

• 67-56-1 methanol 
• 96-36-6 methyl phosphite 
• 87692-15-7 Methyl glyoxalate hydrate 
• 922-68-9 Methyl glyoxylate 
• 868-85-9 Dimethyl phosphite 
• 813-78-5 dimethylphosphoric acid 

Downstream Products

• 116087-97-9 methyl α-(dimethoxyphosphinyl)glycolate benzyl ether 
• 16141-78-9 methyl 2-dimethoxyphosphoryl-2-methoxyacetate 

Relevant articles and documents

Determination of absolute configuration of the phosphonic acid moiety of fosfazinomycins

Fosfazinomycins A and B produced by Streptomyces lavendofoliae share the same phosphonate moiety with one chiral centre of unknown configuration which was determined by synthesising both enantiomers of 2-hydroxy-2-phosphonoacetic acid methyl ester. A chiral cyclic phosphite was reacted with methyl glyoxylate in a Pudovik reaction to give a pair of diastereomeric α- hydroxyphosphonates, which were separated by HPLC. The configurations at C-2 were assigned on the basis of single crystal X-ray structure analysis. Deprotection of these diastereomers furnished the enantiomeric α-hydroxyphosphonic acids, of which the (S)-configured had the same sign of optical rotation as the phosphonic acid moiety of the two fosfazinomycins.

A CONVENIENT METHOD FOR THE SYNTHESIS OF Α-KETOESTERS FROM ALDEHYDES

An efficient two step, two carbon homologation of aldehydes to α-ketoesters is described.