1-deoxy-1-(2,4-difluorophenyl)-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranose

Base Information

• Chemical Name: 1-deoxy-1-(2,4-difluorophenyl)-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranose
• CAS No.: 304436-75-7
• Molecular Formula: C₃₂H₃₀F₂O₆
• Molecular Weight: 548.583
• Mol file: 304436-75-7.mol

Synonyms:1-deoxy-1-(2,4-difluorophenyl)-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranose

Chemical Property of 1-deoxy-1-(2,4-difluorophenyl)-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-deoxy-1-(2,4-difluorophenyl)-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranose

There total 5 articles about 1-deoxy-1-(2,4-difluorophenyl)-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranose 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: 83.4%

4,4'-dimethoxytrityl chloride (40615-36-9) + 1'-deoxy-β-1'-(2,4-difluorophenyl)-D-ribofuranose (263701-23-1) → 1-deoxy-1-(2,4-difluorophenyl)-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranose (304436-75-7)

Guidance literature:

With triethylamine; In pyridine; at 20 ℃; for 2.5h;

DOI:10.1002/1522-2675(20000809)83:8<1791::AID-HLCA1791>3.0.CO;2-K

Reference yield:

2,4-difluorobromobenzene (348-57-2) → 1-deoxy-1-(2,4-difluorophenyl)-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranose (304436-75-7)

Guidance literature:

Multi-step reaction with 4 steps

1: BuLi / diethyl ether; hexane / 3 h / -78 - -30 °C

2: BF₃*Et₂O; Et₃SiH / CH₂Cl₂ / 1 h / -78 °C

3: 99.3 percent / cyclohexene / 20 percent Pd(OH)2/C / ethanol / 3 h / Heating

4: 83.4 percent / Et₃N / pyridine / 2.5 h / 20 °C

With triethylsilane; n-butyllithium; boron trifluoride diethyl etherate; triethylamine; cyclohexene; palladium dihydroxide; In pyridine; diethyl ether; ethanol; hexane; dichloromethane; 1: Dehydrogenation / 2: dehydroxylation / 3: Catalytic hydrogenation / 4: Etherification;

DOI:10.1002/1522-2675(20000809)83:8<1791::AID-HLCA1791>3.0.CO;2-K

Reference yield:

2',3',5'-tri-O-benzyl-1'-deoxy-β-1'-(2,4-difluorophenyl)-D-ribofuranose (304436-74-6) → 1-deoxy-1-(2,4-difluorophenyl)-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranose (304436-75-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 99.3 percent / cyclohexene / 20 percent Pd(OH)2/C / ethanol / 3 h / Heating

2: 83.4 percent / Et₃N / pyridine / 2.5 h / 20 °C

With triethylamine; cyclohexene; palladium dihydroxide; In pyridine; ethanol; 1: Catalytic hydrogenation / 2: Etherification;

DOI:10.1002/1522-2675(20000809)83:8<1791::AID-HLCA1791>3.0.CO;2-K

upstream raw materials:

4,4'-dimethoxytrityl chloride

1'-deoxy-β-1'-(2,4-difluorophenyl)-D-ribofuranose

2,4-difluorobromobenzene

2',3',5'-tri-O-benzyl-1'-deoxy-β-1'-(2,4-difluorophenyl)-D-ribofuranose

Downstream raw materials:

1'-deoxy-β-1'-(2,4-difluorophenyl)-5-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}-D-ribofuranose

2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-1-(2,4-difluorophenyl)-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranose

3'-O-acetyl-1-deoxy-1-(2,4-difluorophenyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-ribofuranose