123155-85-1

Basic information

• Product Name: (±)-[[2-(6-AMino-9H-purin-9-yl)-1-Methylethoxy]Methyl]-phosphonic Acid MonoMethyl Ester
• Synonyms: (±)-[[2-(6-AMino-9H-purin-9-yl)-1-Methylethoxy]Methyl]-phosphonic Acid MonoMethyl Ester;Tenofovir MonoMethyl Ester
• CAS NO: 123155-85-1
• Molecular Formula: C₁₀H₁₆N₅O₄P
• Molecular Weight: 301.238901
• Product Categories: Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;Phosphorylating and Phosphitylating Agents
• Mol File: 123155-85-1.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: (±)-[[2-(6-AMino-9H-purin-9-yl)-1-Methylethoxy]Methyl]-phosphonic Acid MonoMethyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: (±)-[[2-(6-AMino-9H-purin-9-yl)-1-Methylethoxy]Methyl]-phosphonic Acid MonoMethyl Ester(123155-85-1)
• EPA Substance Registry System: (±)-[[2-(6-AMino-9H-purin-9-yl)-1-Methylethoxy]Methyl]-phosphonic Acid MonoMethyl Ester(123155-85-1)

Safety Data

• Hazardous Substances Data: 123155-85-1(Hazardous Substances Data)

Usage

Description

(±)-[[2-(6-Amino-9H-purin-9-yl)-1-Methylethoxy]Methyl]-phosphonic Acid MonoMethyl Ester, also known as Tenofovir MonoMethyl Ester, is an acyclic phosphonate nucleotide analogue derived from the parent compound Tenofovir. It is a light yellow solid with significant antiviral properties, making it a promising candidate for pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
Tenofovir MonoMethyl Ester is used as an anti-HIV agent for its potent activity against the Human Immunodeficiency Virus (HIV). It acts as a reverse transcriptase inhibitor, preventing the viral replication process and thus helping to manage and control the progression of HIV in infected individuals.
Additionally, due to its antiviral properties, Tenofovir MonoMethyl Ester can be used as an antiviral agent in various applications, targeting a range of viral infections beyond HIV. Its effectiveness in inhibiting viral replication makes it a valuable compound in the development of new antiviral therapies and treatments.

Upstream product

• 14047-26-8 6-amino-α-methyl-9H-purine-9-ethanol 
• 80792-13-8 dimethyl <<(p-tolylsulfonyl)oxy>methyl>phosphonate 
• 123156-45-6 N'-[9-(2-Hydroxy-propyl)-9H-purin-6-yl]-N,N-dimethyl-formamidine 

Downstream Products

• 121149-89-1 (+/-)-0-(2-phosphonylmethoxypropyl)adenine 

Relevant articles and documents

PHOSPHONYLMETHOXYALKYL AND PHOSPHONYLALKYL DERIVATIVES OF ADENINE

Analogues of the antivirals (2S)-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine (Ia) and 9-(2-phosphonylmethoxyethyl)adenine (Ib), modified in the alkyl chain, are described.The phosphonylmethoxyalkyl derivatives were prepared by condensation of sodium alkoxides of hydroxyalkyladenines (or their N-protected derivatives) with dimethyl p-toluenesulfonyloxymethanephosphonate (II) followed by alkaline hydrolysis and reactions with halotrimethylsilane, or by reaction of vicinal dihydroxyalkyl derivatives with chloromethanephosphonyl dichloride (XIV) and subsequent cyclization of the intermediates XV in aqueous alkali.In the second case the pure regioisomers were also obtained from substituted dihydroxy derivatives with one free hydroxyl group.The following compounds were prepared in this way: 3-O-methyl ether IIIc and 3-O-octyl ether IVc, 9-(3-phosphonylmethoxypropyl)- (Vc), 9-(4-phosphonylmethoxybutyl)- (Vf), 9-(5-phosphonylmethoxypentyl) (Vi), 9-(2-phosphonylmethoxypropyl)- (VIc), 9-(1-phosphonylmethoxy-3-hydroxy-2-propyl)- (XIIc), 9-(2-methoxy-3-phosphonylmethoxypropyl)- (XIIIc), erythro-9-(2-phosphonylmethoxy-3,4-dihydroxybutyl)- (VIIc), and threo-9-(4-phosphonylmethoxy-2,3-dihydroxybutyl)adenine (IXc) and its enantiomer (Xc). 9-(2-Phosphonylmethoxy-3,3-dihydroxypropyl)adenine (VIII) was obtained by oxidation of VIIc with sodium periodate, 9-(2-phosphonylmethoxyethoxymethyl)adenine (XIc) by reaction of II with sodium salt of 9-(2-hydroxyethoxymethyl)adenine (XIa). 9-(1,2-Dihydroxy-2-methyl-3-propyl)adenine 1- and 2-phosphonylmethyl ether (XVIb), 9-(3,4-dihydroxybutyl)adenine 3- and 4-phosphonylmethyl ether (XVIIb) and 9-(2,3-dihydroxybutyl)adenine 2- and 3-phosphonylmethyl ether (XVIIIb) were prepared by reaction chloromethanephosphonyl dichloride (XIV) followed by alkaline treatment.Analogous reaction was also employed in the preparation of regioisomerically pure 1-phosphonylmethyl ethers of 9-(1,2-dihydroxy-3-butyl)adenine (XXIV), 9-(1,2-dihydroxy-2-methyl-3-propyl)adenine (XVIb) and 9-(1,2-dihydroxy-3-nonyl)adenine (XXV).Alkylation of adenine with diethyl chloromethoxymethanephosphonate (XXVII) followed by hydrolysis afforded 9-(phosphonylmethoxymethyl)adenine (XXVIIIb). 9-(Phosphonylmethyl)adenine (XLI) was obtained by condensation of adenine with compound II.Conversion of 9-(ω-hydroxyalkyl)adenines into the ω-halogenoalkyl derivatives followed by reaction with trialkyl phosphite and cleavage was used in the preparation of 9-(2-phosphonylethyl)adenine (XXXIVa), 9-(4-phosphonylbutyl)adenine (XXXIVb) and 9-(2-phosphonylethoxymethyl)adenine (XXXIX). 9-(2-Phosphonyl-2-hydroxyethyl)adenine (Lc) and 9-(3-phosphonyl-3-hydroxypropyl)adenine (Lb) were synthesized by treatment of ω-(adenin-9-yl)alkanals with dialkyl phosphite and subsequent cleavage with halogenotrimethylsilane; the same procedure converted 9-(2-oxopropyl)adenine (XLVIIIa) into 9-(2-phosphonyl-2-hydroxypropyl)adenine (La).