117286-92-7

Usage

Uses

Used in Biochemical Research:
Diisopropyl(phosphoryl)-trans-4-hydroxyprolin is utilized as a research tool in biochemical studies for understanding the role of phosphorylated amino acids in cellular signaling pathways. Its unique structure allows scientists to investigate the effects of phosphorylation on protein function and interactions.
Used in Pharmaceutical Development:
In the pharmaceutical industry, Diisopropyl(phosphoryl)-trans-4-hydroxyprolin serves as a potential drug target or lead compound for the development of therapeutics aimed at treating diseases such as cancer and neurodegenerative disorders. Diisopropyl(phosphoryl)-trans-4-hydroxyprolin's ability to modulate signaling pathways involved in these diseases makes it a valuable candidate for further exploration and optimization.
Used in Drug Delivery Systems:
Diisopropyl(phosphoryl)-trans-4-hydroxyprolin may also be employed in the design of drug delivery systems to improve the bioavailability and therapeutic efficacy of drugs targeting phosphorylated amino acids. Diisopropyl(phosphoryl)-trans-4-hydroxyprolin's enhanced solubility and stability can contribute to the development of more effective drug formulations.
Used in Diagnostic Applications:
Furthermore, Diisopropyl(phosphoryl)-trans-4-hydroxyprolin could be applied in diagnostic assays to detect and monitor diseases related to abnormal phosphorylation events. Its specific interactions with biological targets can be harnessed to develop sensitive and selective diagnostic tools.

InChI:InChI=1/C11H22NO6P/c1-7(2)17-19(16,18-8(3)4)12-6-9(13)5-10(12)11(14)15/h7-10,13H,5-6H2,1-4H3,(H,14,15)/t9-,10+/m1/s1

Upstream product

• 51-35-4 4R-4-hydroxyproline 
• 2574-25-6 Diisopropyl chlorophosphate 
• 1809-20-7 diisopropyl hydrogenphosphonate 

Downstream Products

• 219909-83-8 (2S-cis)-3-[[(4-mercapto-2-pyrrolidinyl)carbonyl]amino]benzoic acid monohydrochloride 
• 266337-24-0 C₂₄H₃₃NO₉P₂S 
• 220031-86-7 3-{[(2S,4S)-1-(Diisopropoxy-phosphoryl)-4-mercapto-pyrrolidine-2-carbonyl]-amino}-benzoic acid 
• 444057-64-1 (2S)-cis-3-[[(4-mercapto-2-pyrrolidinyl)carbonyl]amino]benzoic acid monohydrochloride disulfide 
• 266337-23-9 (2S-trans)-1-[bis(1-methylethoxy)phosphinyl]tetrahydro-4-hydroxy-2H-pyrrole-2-carboxylic acid diphenylphosphinyl ester 

Relevant academic research and scientific papers

Preparation method of ertapenem side chain synthetic intermediate

The invention discloses a novel synthesis method of an ertapenem side chain synthesis intermediate N-(O, O-diisopropyl phosphoryl)-trans-4-hydroxy-L-proline, which comprises the following steps: in the presence of a phase transfer catalyst, adding diisopropyl phosphite and the phase transfer catalyst into 4R-hydroxy-L-proline serving as a raw material under alkaline conditions, dropwise adding a sodium hypochlorite/sodium hydroxide mixed solution to carry out a one-pot reaction so as to prepare N-(O, O-diisopropyl phosphoryl)-trans-4-hydroxy-L-proline. According to the present invention, withthe process, the excellent target product yield and the excellent target product purity can be obtained, the reaction temperature condition does not need to be strictly controlled, the energy consumption cost is saved, the operation is simplified, and the method is suitable for industrial production.

Preparation method of N-(O, O-diisopropylphosphoryl)-trans-4-hydroxy-L-proline

The invention belongs to the technical field of medical intermediates and specifically relates to a preparation method of N-(O, O-diisopropylphosphoryl)-trans-4-hydroxy-L-proline. The preparation method of the N-(O, O-diisopropylphosphoryl)-trans-4-hydroxy-L-proline comprises the steps of adding L-hydroxyproline to purified water; cooling an obtained mixture; beginning to drip 25% sodium hydroxidesolution into the obtained mixture while stirring the obtained mixture; regulating pH value of a mixture to 9.0-10; stirring the mixture to a clarified state for future use; dripping sodium hypochlorite into diisopropyl phosphite at a low temperature; rapidly stirring an obtained mixture and preserving the heat of the obtained mixture for reaction; after it is detected in gas phase that DIPP reaction is completely finished, adding sodium hydrogen sulfite to a reaction product; adding prepared L-hydroxyproline solution to the reaction product; controlling the pH value of a reaction system so that the reaction system is kept to be alkaline; heating and preserving the heat of the reaction system till the pH value of a reaction liquid is not changed; using halogenated hydrocarbon to wash thereaction system and layering the reaction system; regulating an aqueous phase to be acidic by using hydrochloric acid; adding an ester organic solvent to extract the aqueous phase; decompressing and concentrating an organic phase; carrying out cooling and suction filtration on the decompressed and concentrated organic phase; and drying the cooled and sucked-filtered organic phase at 40 degrees centigrade to obtain white powder solids. The preparation method of the N-(O, O-diisopropylphosphoryl)-trans-4-hydroxy-L-proline, provided by the invention, has the advantages of less side reaction, highyield, high purity and mild reaction condition.

Efficient one-pot synthesis of the 2-aminocarbonylpyrrolidin-4-ylthio-containing side chain of the new broad-spectrum carbapenem antibiotic ertapenem.

An efficient synthesis of the 2-aminocarbonylpyrrolidin-4-ylthio containing side chain of ertapenem (MK-0826) is described. Starting material N-(O,O-diisopropyl phosphoryl)-trans-4-hydroxy-L-proline is converted in a one-pot process to (2S)-cis-3-[[(4-mercapto-2-pyrrolidinyl)carbonyl]amino]benzoic acid monohydrochloride in 70-75% overall yield via a series of six reactions. The development of each of these reactions and the isolation of the product is discussed in detail.

A practical preparation of diisopropyl phosphoryl protected amino acids

N-Diisopropyl phosphoryl protected amino acids can be prepared in high yield and without racemization by slow addition of sodium hypochlorite to a solution of the amino acid and diisopropylphosphite in water while carefully maintaining a constant pH via t