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

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 180587-75-1 differently. You can refer to the following data:
1. A acyclic phosphonate nucleotide
2. A acyclic phosphonate nucleotide.

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

• 3084-40-0 diethyl (1-hydroxymethyl)phosphonate 
• 31618-90-3 diethyl (p-toluenesulfonyloxymethane)phosphonate 
• 66224-66-6 adenine 
• 16606-55-6 (R)-1,2-propylene carbonate 
• 64-17-5 ethanol 
• 342631-41-8 9-[(R)-2-[[(S)-[bis(phenoxy)phosphinyl]]methoxy]propyl]adenine 
• 14047-28-0 (R)-9-(2-hydroxypropyl)adenine 
• 114108-84-8 diethyl <<(methylsulfonyl)oxy>methyl>phosphonate 
• 4331-29-7 4-aminobenzimidazole 
• 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 

Downstream Products

• 147127-20-6 tenofovir 
• 201341-05-1 tenofovir disoproxil 
• 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 
• 1354647-85-0 (R)-9-[2-(pivaloyloxymethyl)-(isopropoxycarbonyloxymethyl)phosphonoylmethoxypropyl]adenine p-toluenesulfonate 
• 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.

Method for preparing tenofovir disoproxil

The invention discloses a method for preparing tenofovir disoproxil and relates to the field of preparation of tenofovir disoproxil. The method for preparing the tenofovir disoproxil specifically comprises the following steps: A) preparing (R)-9-(2-hydroxypropyl) adenine; B) preparing (R)-9-(2-phosphonic acid methoxy-propyl) adenine di(ethyl) ester; C) preparing tenofovir; D) preparing tenofovir disoproxil; and E) carrying out finished product detection and inspection. Compared with the prior art, the method has the beneficial effects that while the medicine effect of the tenofovir disoproxilis ensured, the reaction steps are simplified, the yield is increased, the conversion rates of intermediates (R)-9-(2-hydroxypropyl) adenine, (R)-9-(2-phosphonic acid methoxy-propyl) adenine di(ethyl)ester and tenofovir reach 75%, 63.2% and 74.3% respectively, and the total yield of the tenofovir disoproxil is as high as 62.4% finally.