180587-75-1

Basic information

• Product Name: (R)-9-[2-(DIETHYLPHOSPHONOMETHOXY)PROPYL] ADENINE
• Synonyms: (R)-9-[2-(DIETHYLPHOSPHONOMETHOXY)PROPYL] ADENINE;(R)-diethyl (1-(6-aMino-9H-purin-9-yl)propan-2-yloxy)Methylphosphonate;[[(1R)-2-(6-AMino-9H-purin-9-yl)-1-Methylethoxy]Methyl]phosphonic Acid Diethyl Ester;P-[[(1R)-2-(6-AMino-9H-purin-9-yl)-1-Methylethoxy]Methyl]phosphonic Acid Diethyl Ester;Diethyl Tenofovir;(R)-9-[2-(Diethylphosphonomethoxy)propy] Adenine;Tenofovir disoproxil Impurity V
• CAS NO: 180587-75-1
• Molecular Formula: C₁₃H₂₂N₅O₄P
• Molecular Weight: 343.32
• Product Categories: Chiral Reagents;Bases & Related Reagents;Nucleotides
• Mol File: 180587-75-1.mol
• Article Data: 50

Chemical Properties

• Melting Point: 107-109°C
• Boiling Point: 532.44°C at 760 mmHg
• Flash Point: 275.81°C
• Appearance: /
• Density: 1.423g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.611
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.21±0.10(Predicted)
• CAS DataBase Reference: (R)-9-[2-(DIETHYLPHOSPHONOMETHOXY)PROPYL] ADENINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-9-[2-(DIETHYLPHOSPHONOMETHOXY)PROPYL] ADENINE(180587-75-1)
• EPA Substance Registry System: (R)-9-[2-(DIETHYLPHOSPHONOMETHOXY)PROPYL] ADENINE(180587-75-1)

Safety Data

• Hazardous Substances Data: 180587-75-1(Hazardous Substances Data)

Usage

Description

(R)-9-[2-(DIETHYLPHOSPHONOMETHOXY)PROPYL] ADENINE, also known as an acyclic phosphonate nucleotide, is a white solid with unique chemical properties. It is a synthetic compound that has been developed for its potential applications in various fields due to its distinct structure and characteristics.

Uses

(R)-9-[2-(DIETHYLPHOSPHONOMETHOXY)PROPYL] ADENINE is used as a pharmaceutical compound for its potential therapeutic applications.
Used in Pharmaceutical Industry:
(R)-9-[2-(DIETHYLPHOSPHONOMETHOXY)PROPYL] ADENINE is used as a therapeutic agent for its potential to target specific biological processes and pathways. Its acyclic phosphonate nucleotide structure allows it to interact with cellular components, making it a promising candidate for the development of new drugs and therapies.
Additionally, due to its unique chemical properties, (R)-9-[2-(DIETHYLPHOSPHONOMETHOXY)PROPYL] ADENINE may also be used in other industries, such as:
Used in Chemical Research Industry:
(R)-9-[2-(DIETHYLPHOSPHONOMETHOXY)PROPYL] ADENINE is used as a research compound for studying its interactions with various biological targets and understanding its potential applications in drug discovery and development.
Used in Material Science Industry:
The white solid nature of (R)-9-[2-(DIETHYLPHOSPHONOMETHOXY)PROPYL] ADENINE may also find applications in the development of new materials with specific properties, such as in the creation of advanced coatings or other industrial applications where its unique characteristics can be utilized.

InChI:InChI=1/C13H22N5O4P/c1-4-21-23(19,22-5-2)9-20-10(3)6-18-8-17-11-12(14)15-7-16-13(11)18/h7-8,10H,4-6,9H2,1-3H3,(H2,14,15,16)/t10-/m1/s1

Upstream product

• 31618-90-3 diethyl (p-toluenesulfonyloxymethane)phosphonate 
• 14047-28-0 (R)-9-(2-hydroxypropyl)adenine 
• 64-17-5 ethanol 
• 342631-41-8 9-[(R)-2-[[(S)-[bis(phenoxy)phosphinyl]]methoxy]propyl]adenine 
• 114108-84-8 diethyl <<(methylsulfonyl)oxy>methyl>phosphonate 
• 4331-29-7 4-aminobenzimidazole 
• 16606-55-6 (R)-1,2-propylene carbonate 
• 66224-66-6 adenine 
• 1493808-01-7 (R)-1-(6-chloropurine-9-yl)-2-(diethoxyphosphorylmethoxy)propane 
• 105970-02-3 1-(6-amino-9H-purin-9-yl)propan-2-one 
• 106938-62-9 (diethoxyphosphinyl)methyl trifluoromethanesulfonate 
• 213694-15-6 1-(6-iodo-9H-purin-9-yl)propan-2-one 
• 100682-42-6 1-(6-chloro-9H-purin-9-yl)-2-propanone 
• 14047-27-9 (S)-1-(6-amino-9H-purin-9-yl) propan-2-ol 

Downstream Products

• 147127-20-6 tenofovir 
• 201341-05-1 tenofovir disoproxil 
• 1354647-85-0 (R)-9-[2-(pivaloyloxymethyl)-(isopropoxycarbonyloxymethyl)phosphonoylmethoxypropyl]adenine p-toluenesulfonate 
• 1432630-26-6 tenofovir disoproxil fumarate 
• 211364-69-1 Tenofovir mono-POC 
• 1246812-40-7 propan-2-yl {[(propan-2-yloxy)carbonyl]oxy}methyl {[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methanephosphonate 
• 202138-50-9 tenofovir disoproxyl fumarate 
• 1244022-55-6 C₁₅H₂₄N₅O₈P 
• 1244022-53-4 C₂₀H₃₂N₅O₁₁P 

Relevant articles and documents

Preparation method of nucleoside phosphate prodrug

The invention belongs to the field of pharmaceutical chemicals, and relates to a preparation method of a nucleoside phosphate prodrug. A diphenol phosphate intermediate A and an alcohol compound B are subjected to a transesterification reaction to obtain the nucleoside phosphate prodrug. According to the method, rapid synthesis of different nucleoside prodrugs is achieved through exchange of the base-catalyzed nucleoside diphenyl phosphate intermediate and alcohol, synthesis of a target compound is achieved through one-step reaction, meanwhile, use of strong acid and high-toxicity chlorides is avoided, the safety of generation can be improved, the cost is reduced, and emission of three wastes is reduced.

Synthesis process of antiviral drug

The invention discloses a synthesis process of an antiviral drug. The process comprises the following steps: reacting adenine (II) with (R)- propylene carbonate (III) to prepare a compound IV, carrying out alkylation reaction on the compound IV and a compound V to prepare a compound VI, and carrying out esterolysis reaction to prepare a compound VII; and carrying out esterification reaction on theprepared compound VII and chloromethyl isopropyl carbonate, and salifying with fumaric acid to prepare the final product tenofovir disoproxil fumarate (I). The synthetic route is simple, the reactionconditions are mild, the generation of impurities is reduced, the total yield and purity of the product are improved, and the method is suitable for industrial production.

Tenofovir disoproxil fumarate analog preparation method

The present invention discloses a tenofovir disoproxil fumarate analog preparation method, which comprises: carrying out a substitution reaction on adenine as a raw material and (R)-propylene carbonate in the presence of an alkali, carrying out a substitution reaction with (diethoxyphosphoryl)methyl-4-methylbenzenesulfonate, hydrolyzing with a concentrated hydrochloric acid solution, crystallizingto obtain anhydrous tenofovir, carrying out a reaction on the anhydrous tenofovir and chloromethyl isopropyl carbonate to obtain tenofovir monoester, and carrying out a reaction with 2-bromopropane to obtain the target compound. According to the present invention, the selected starting raw materials are inexpensive and easy to obtain, the process is simple, and the material utilization rate and total yield are improved; and the intermediate of the method is purified by re-crystallization, such that the yield is high, and the purity is high.