168427-35-8

Basic information

• Product Name: 1-Methyl-3,5-bis-O-(2,4-dichlorobenzyl)-alpha-D-ribofuranoside
• Synonyms: Methyl 3,5-Bis-O-(2,4-dichlorobenzyl)-α-D-ribofuranoside;Methyl 3,5-di-O-(2,4-dichlorobenzyl)-a-D-ribofuranoside;1-O-Methyl 3,5-Bis-O-(2,4-dichlorobenzyl)-α-D-ribofuranoside;Methyl 3,5-Bis-O-[(2,4-dichlorophenyl)Methyl]-α-D-ribofuranoside;1-Methyl-3,5-bis-O-(2,4-dichlorobenzyl)-alpha-D-ribofuranoside
• CAS NO: 168427-35-8
• Molecular Formula: C₂₀H₂₀Cl₄O₅
• Molecular Weight: 482.18
• Product Categories: Aromatics;Carbohydrates & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 168427-35-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 584.13 °C at 760 mmHg
• Flash Point: 307.071 °C
• Appearance: /
• Density: 1.46
• Refractive Index: 1.628
• PKA: 12.91±0.70(Predicted)
• CAS DataBase Reference: 1-Methyl-3,5-bis-O-(2,4-dichlorobenzyl)-alpha-D-ribofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-3,5-bis-O-(2,4-dichlorobenzyl)-alpha-D-ribofuranoside(168427-35-8)
• EPA Substance Registry System: 1-Methyl-3,5-bis-O-(2,4-dichlorobenzyl)-alpha-D-ribofuranoside(168427-35-8)

Safety Data

• Hazardous Substances Data: 168427-35-8(Hazardous Substances Data)

Usage

Description

1-Methyl-3,5-bis-O-(2,4-dichlorobenzyl)-alpha-D-ribofuranoside is a complex organic compound that serves as a crucial intermediate in the synthesis of nucleoside compounds and their derivatives. It is characterized by its unique chemical structure, which includes a ribofuranoside core with two 2,4-dichlorobenzyl groups attached to specific positions. 1-Methyl-3,5-bis-O-(2,4-dichlorobenzyl)-alpha-D-ribofuranoside plays a significant role in the development of pharmaceuticals targeting specific viral infections.

Uses

1. Used in Pharmaceutical Industry:
1-Methyl-3,5-bis-O-(2,4-dichlorobenzyl)-alpha-D-ribofuranoside is used as an intermediate in the synthesis of nucleoside compounds for the development of antiviral drugs. Its application is primarily focused on the treatment or prophylaxis of infections caused by the SARS virus. The compound's unique structure allows for the creation of derivatives that can effectively target and inhibit the replication of the SARS virus, providing a potential therapeutic solution for individuals affected by this infection.
2. Used in Antiviral Research:
In the field of antiviral research, 1-Methyl-3,5-bis-O-(2,4-dichlorobenzyl)-alpha-D-ribofuranoside is utilized as a key component in the design and synthesis of novel nucleoside analogs. These analogs have the potential to interfere with the life cycle of the SARS virus, thereby inhibiting its replication and spread within the host. The compound's role in this process is vital, as it forms the basis for the development of new antiviral agents that can combat SARS and related viral infections.
3. Used in Drug Development for SARS Treatment and Prophylaxis:
1-Methyl-3,5-bis-O-(2,4-dichlorobenzyl)-alpha-D-ribofuranoside is also used in the development of drugs aimed at treating or preventing SARS infections. By incorporating this compound into the synthesis of nucleoside derivatives, researchers can create new drugs that target the SARS virus specifically, offering a more effective treatment option for patients. Additionally, these derivatives can be used as prophylactic agents to protect individuals from contracting the virus in the first place.

InChI:InChI=1/C20H19Cl4O5/c1-20(26)19(25)18(28-9-12-3-5-14(22)7-16(12)24)17(29-20)10-27-8-11-2-4-13(21)6-15(11)23/h2-7,17-19,25H,8-10H2,1H3/q-1/t17-,18-,19-,20+/m1/s1

Upstream product

• 7473-45-2 1-O-methyl-D-ribofuranose 
• 168427-36-9 2-O-acetyl-3,5-bis-O-(2,4-dichlorophenylmethyl)-1-O-methyl-α-D-ribofuranose 
• 50-69-1 D-ribose 
• 94-99-5 2,4-Dichlorobenzyl chloride 
• 1824-96-0 methyl ribofuranoside 
• 677299-16-0 (2R,3R,4R)-3,4-bis((2,4-dichlorobenzyl)oxy)-2-(((2,4-dichlorobenzyl)oxy)methyl)-5-methoxytetrahydrofuran 
• 163759-40-8 methyl 2,3,5-tris-O-(2,4-dichlorobenzyl)-β-D-ribofuranoside 

Downstream Products

• 55486-09-4 2'-O-Methyl-5-methyluridine 
• 153631-19-7 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-5-methyluridine 
• 153631-20-0 (2R,3R,4R,5R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-((tert-butyldimethylsilyl)oxy)-5-(5-methyl-2,4-dioxo-3,4-dihyd ropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite 
• 163759-49-7 2'-O-(2-methoxyethyl)-5-methyluridine 
• 168427-74-5 2'-O-(2-methoxyethyl)adenosine 
• 168427-64-3 1-[(2R,3R,4R,5R)-4-(2,4-Dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-methoxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 168427-65-4 1-[(2R,3R,4R,5R)-4-(2,4-Dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-propoxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 168427-66-5 1-[(2R,3R,4R,5R)-4-(2,4-Dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-isopropoxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 182495-86-9 1-{(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-propoxy-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione 
• 168427-71-2 9-<3',5'-Bis-O-(2,4-dichlorobenzyl)-β-D-ribofuranosyl>-6-methoxy-9H-purin 
• 163759-43-1 1-<2'-O-Acetyl-3',5'-bis-O-(2,4-dichlorobenzyl)-β-D-ribofuranosyl>thymin 
• 163759-50-0 5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(2-methoxyethyl)-5-methyluridine 
• 168427-70-1 9-<2'-O-Acetyl-3',5'-bis-O-(2,4-dichlorobenzyl)-β-D-ribofuranosyl>-6-chloro-9H-purin 
• 168427-97-2 1-[(2R,3R,4R,5R)-4-(2,4-Dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-((R)-2-methoxy-propoxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 

Relevant articles and documents

NUCLEOSIDE DERIVATIVES AS INHIBITORS OF RNA-DEPENDENT RNA VIRAL POLYERMASE

The present invention provides nucleoside compounds and certain derivatives thereof which are inhibitors of RNA-dependent RNA viral polymerase. These compounds are inhibitors of RNA-dependent RNA viral replication and are useful for the treatment of RNA-dependent RNA viral infection. They are particularly useful as inhibitors of hepatitis C virus (HCV) NS5B polymerase, as inhibitors of HCV replication, and/or for the treatment of hepatitis C infection. The invention also describes pharmaceutical compositions containing such nucleoside compounds alone or in combination with other agents active against RNA-dependent RNA viral infection, in particular HCV infection. Also disclosed are methods of inhibiting RNA-dependent RNA polymerase, inhibiting RNA-dependent RNA viral replication, and/or treating RNA-dependent RNA viral infection with the nucleoside compounds of the present invention.

An efficient approach for the synthesis of 1′-O-α-methyl pyrrolo[2,3-d]pyrimidine isonucleosides

A series of novel 1′-O-methyl isonucleosides were efficiently and stereoselectively synthesized with 1,2,3,5-tetra-O-acetyl-D-ribofuranose as the starting material. The key steps include regioselective and stereoselective deprotection of the 2,4-dichlorobenzyl group at C2, triflation, and substitution with appropriate nucleobases using cesium carbonate as the base. Removal of the residual 2,4-dichlorobenzyl groups and subsequent transformation afforded the title compounds in 30-37% overall yield. The products represent a new type of isonucleosides with 1-O-substitution. Georg Thieme Verlag Stuttgart New York.

Inhibiting Coronaviridae viral replication and treating Coronaviridae viral infection with nucleoside compounds

Infection by a Coronaviridae virus (e.g., a coronavirus) and/or illness due to a Coronaviridae virus are treated or protected against by administration of a therapeutically or prophylactically effective amount of certain nucleoside compounds and derivatives thereof, either alone or in a composition comprising the nucleoside compound or its derivative and a pharmaceutically acceptable carrier. In addition, replication of a Coronaviridae virus is inhibited by administration of the nucleoside compounds and derivatives thereof, either alone or in pharmaceutical compositions. The nucleosides are particularly suitable for use in treating or prophylaxis of an infection by the SARS virus and/or in treating or prophylaxis of SARS, and for use in inhibiting replication of the SARS virus. The nucleoside compounds and derivatives can optionally be administered in combination with other agents active against the Coronaviridae virus and/or an illness due to the virus. The nucleoside compounds are also for use in the manufacture of medicaments for the inhibition of Coronaviridae virus replication, for the treatment or prophylaxis of Coronaviridae virus infection, and/or for the treatment or prophylaxis of an illness due to a Coronaviridae virus (e.g., the SARS virus). In addition, the compounds are for use as medicaments for the inhibition of Coronaviridae virus replication, for the treatment or prophylaxis of Coronaviridae virus infection, and/or for the treatment or prophylaxis of an illness due to a Coronaviridae virus.