86357-14-4

Basic information

• Product Name: N-[9-[[2-(Acetyloxy)-1-[(acetyloxy)methyl]ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]acetamide
• Synonyms: N-[9-[[2-(Acetyloxy)-1-[(acetyloxy)methyl]ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]acetamide;Triacetylganciclovir;N-Acetyl-di-O-acetyl Ganciclovir;Three acetyl ganciclovir;2-((2-Acetamido-6-oxo-1H-purin-9(6H)-yl)methoxy)propane-1,3-diyl diacetate;Acetamide,N-[9-[[2-(acetyloxy)-1-[(acetyloxy)methyl]ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]-
• CAS NO: 86357-14-4
• Molecular Formula: C₁₅H₁₉N₅O₇
• Molecular Weight: 381.34
• EINECS: 1312995-182-4
• Product Categories: Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals
• Mol File: 86357-14-4.mol

Chemical Properties

• Melting Point: 174 °C
• Appearance: light brown solid
• Density: 1.50
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 8.74±0.20(Predicted)
• CAS DataBase Reference: N-[9-[[2-(Acetyloxy)-1-[(acetyloxy)methyl]ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[9-[[2-(Acetyloxy)-1-[(acetyloxy)methyl]ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]acetamide(86357-14-4)
• EPA Substance Registry System: N-[9-[[2-(Acetyloxy)-1-[(acetyloxy)methyl]ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]acetamide(86357-14-4)

Safety Data

• Hazardous Substances Data: 86357-14-4(Hazardous Substances Data)

Usage

Chemical Properties

Light Brown Solid

Uses

Ganciclovir derivative.

Upstream product

• 86357-13-3 2-(acetoxymethoxy)-1,3-propanediyl diacetate 
• 19962-37-9 N-(6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide 
• 105-70-4 2-hydroxypropane-1,3-diyl diacetate 
• 3056-33-5 2,9-diacetylguanine 
• 82410-32-0 ganciclovir 
• 108-24-7 acetic anhydride 
• 86357-17-7 7-(1,3-diacetoxy-2-propoxymethyl)-N²-acetylguanine 

Downstream Products

• 82410-32-0 ganciclovir 
• 96551-29-0 ganciclovir 
• 88110-89-8 9-<(1-acetoxy-2-hydroxymethyl)ethoxymethyl>guanine 

Relevant articles and documents

Method for synthesizing acyclovir and ganciclovir by carbon-hydrogen bond activation

The invention discloses a method for synthesizing acyclovir and ganciclovir by carbon-hydrogen bond activation and belongs to the field of organic synthesis. The method comprises that inexpensive guanine as a raw material undergoes methyl protection on 9th NH, a high-valent iodine reagent and monoacetyl-protected ethylene glycol or 1, 2-isopropylidene-protected glycerol are added into the raw material under catalysis of palladium acetate, the mixture undergo a heating reaction to produce acetyl-protected acyclovir or acetyl-protected ganciclovir, and the acetyl group is removed by an inorganicalkali alcohol solution so that acyclovir and ganciclovir are obtained. The method utilizes cheap and easily available raw materials, prevents use risk and corrosive reagents, has the advantages of short reaction route, simple operation, high atomic economy and high total product yield, provides a novel synthesis route of acyclovir and ganciclovir and has a potential application prospect.

Preparation method of ganciclovir

The invention discloses a preparation method of ganciclovir, and belongs to the technical field of medicine synthesis. The method comprises the following steps: condensing 1, 3-diacetyl oxygen-2-(acetoxymethoxyl) propane, 2, 9-diacetylguanine and a catalyst in a microwave reactor to obtain triacetyl ganciclovir; hydrolyzing a coarse triacetyl ganciclovir product in the microwave reactor to obtaina coarse ganciclovir product; and purifying to obtain high-purity ganciclovir. According to the method, the microwave reactor is used, so that the reaction selectivity is high; the raw material diacetylguanine residues are few, so that the conversion rate is high; the shortages of change of rate of post-process isomers are removed; the quality of an obtained intermediate is high; the operation steps are decreased; the cost is reduced; and moreover, the synthesizing quality of ganciclovir is improved; and the production efficiency is high.

GANCICLOVIR DERIVATIVES FOR MODULATING INNATE AND ADAPTIVE IMMUNITY AND FOR USE IN IMMUNOTHERAPY

Compositions and methods for modulating innate and adaptive immunity and for use in immunotherapy are disclosed. In particular, the invention relates to novel ganciclovir derivatives and methods of using them for the treatment of immune-related disorders, including inflammation, autoimmunity, and infections, and neurological disorders, and cancer.

PROCESS FOR THE SYNTHESIS OF GANCICLOVIR

The present invention relates to an industrial useful process for the synthesis of antiviral compound, ganciclovir.

PROCESS FOR THE PREPARATION OF GANCICLOVIR

The present invention relates to a process for the preparation of N2-Acetyl-9-(1,3-diacetoxy-2-propoxymethyl) guanine, referred to here as N-9 alkylated isomer of structural formula I, and to the use of this compound as an intermediate for the preparation of antiviral compound, ganciclovir.

A facile synthesis of 9-(1,3-dihydroxy-2-propoxymethyl)guanine (ganciclovir) from guanosine

The potent and selective antiviral drug ganciclovir (6) has been synthesized in two steps via transpurination of fully acetylated guanosine (1) in the presence of 1,3-diacetoxy-2-(acetoxymethoxy)propane (2), followed by deacetylation in aqueous ammonia. The transpurination reaction also provides valuable side products, tetra-O-acetyl-β-D-ribofuranose (5) and the 7-regioisomer of triacetylganciclovir (4); the latter product can be converted to the desired 9-isomer in a thermal 7 ? 9 isomerization.

Syntheses of acyclic guanine nucleosides

A method is provided for the synthesis of synthesis of acyclic purine nucleosides, particularly 9-(2-hydroxyethoxymethyl)-guanine (acyclovir) and 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine ("DHPG") where the N2,N9 -diprotected guanine is reacted with CH3 C(O)OCH2 O(CH2)2)OC(O)CH3 or diacetoxypropane, respectively, in the presence of a mixture of an acid and acetic anhydride, or in the presence of an acid, where the acid can be phosphoric acid or polyphosphoric acid.

Anti-viral guanine compounds

9-(1,3-Dihydroxy-2-propoxymethyl)guanine and 9-(2,3-dihydroxy-1-propoxymethyl)guanine have been found to have potent anti-viral activity against herpes viruses. These compounds, their acyl derivatives, their phosphate derivatives and their pharmaceutically acceptable salts, pharmaceutical formulations containing these compounds, the treatment of DNA viral or herpes viral infections with these compounds, method of preparing these compounds, and novel intermediates useful in their preparation are all disclosed. The compounds may be prepared by reaction of the appropriate acetoxymethyl ether with diacetylguanine, followed by deprotection. The acetoxymethyl ethers may be obtained by reaction of glycerol formal with acetic anhydride in the presence of a catalyst.