1-Methyl-3,5-bis-O-(2,4-dichlorobenzyl)-alpha-D-ribofuranoside

Base Information

• Chemical Name: 1-Methyl-3,5-bis-O-(2,4-dichlorobenzyl)-alpha-D-ribofuranoside
• CAS No.: 168427-35-8
• Molecular Formula: C20H20Cl4O5
• Molecular Weight: 482.188
• Mol file: 168427-35-8.mol

Synonyms:(2S,3R,4S,5R)-4-[(2,4-Dichlorobenzyl)oxy]-5-{[(2,4-dichlorobenzyl)oxy]methyl}-3-hydroxy-2-methyltetrahydrofuran-2-olate;

Chemical Property of 1-Methyl-3,5-bis-O-(2,4-dichlorobenzyl)-alpha-D-ribofuranoside

Chemical Property:

• Refractive Index: 1.628
• Boiling Point: 584.13 °C at 760 mmHg
• PKA: 12.91±0.70(Predicted)
• Flash Point: 307.071 °C
• PSA: 57.15000
• Density: 1.5 g/cm³
• LogP: 5.13440

Purity/Quality:

99% ^*data from raw suppliers

Methyl3,5-Bis-O-(2,4-dichlorobenzyl)-α-D-ribofuranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1-Methyl-3,5-bis-O-(2,4-dichlorobenzyl)-alpha-D-ribofuranoside is an intermediate in the synthesis of nucleoside compounds and derivatives 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.

Technology Process of 1-Methyl-3,5-bis-O-(2,4-dichlorobenzyl)-alpha-D-ribofuranoside

There total 8 articles about 1-Methyl-3,5-bis-O-(2,4-dichlorobenzyl)-alpha-D-ribofuranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

(2R,3R,4R)-3,4-bis((2,4-dichlorobenzyl)oxy)-2-(((2,4-dichlorobenzyl)oxy)methyl)-5-methoxytetrahydrofuran (677299-16-0) → (3R,4S,5R)-4-((2,4-dichlorobenzyl)oxy)-5-(((2,4-dichlorobenzyl)oxy)methyl)-2-methoxytetrahydrofuran-3-ol (168427-35-8)

Guidance literature:

With tin(IV) chloride; In dichloromethane; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acsmedchemlett.6b00270

Reference yield: 85.0%

methyl 2,3,5-tris-O-(2,4-dichlorobenzyl)-β-D-ribofuranoside (163759-40-8) → (3R,4S,5R)-4-((2,4-dichlorobenzyl)oxy)-5-(((2,4-dichlorobenzyl)oxy)methyl)-2-methoxytetrahydrofuran-3-ol (168427-35-8)

Guidance literature:

With tin(IV) chloride; In dichloromethane; at 0 ℃; for 28h; regioselective reaction; Inert atmosphere;

DOI:10.1055/s-0030-1259961

Reference yield:

2-O-acetyl-3,5-bis-O-(2,4-dichlorophenylmethyl)-1-O-methyl-α-D-ribofuranose (168427-36-9) → (3R,4S,5R)-4-((2,4-dichlorobenzyl)oxy)-5-(((2,4-dichlorobenzyl)oxy)methyl)-2-methoxytetrahydrofuran-3-ol (168427-35-8)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 0.75h;

upstream raw materials:

methyl 2,3,5-tris-O-(2,4-dichlorobenzyl)-β-D-ribofuranoside

(2R,3R,4R)-3,4-bis((2,4-dichlorobenzyl)oxy)-2-(((2,4-dichlorobenzyl)oxy)methyl)-5-methoxytetrahydrofuran

methyl ribofuranoside

2,4-Dichlorobenzyl chloride

Downstream raw materials:

methyl 3,5-bis-O-(2,4-dichlorobenzyl)-2-O-(trifluoromethylsulfonyl)-α-D-ribofuranoside

3-[methyl α-D-arabinofuranosid-2-yl]adenine

4-chloro-7-[methyl 3,5-bis-O-(2,4-dichlorobenzyl)-α-D-arabinofuranosid-2-yl]-7H-pyrrolo[2,3-d]pyrimidine

9-[methyl 3,5-bis-O-(2,4-dichlorobenzyl)-α-D-arabinofuranosid-2-yl]adenine