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

Base Information

• Chemical Name: 2',3',5'-tri-O-benzyl-1'-deoxy-β-1'-(2,4-difluorophenyl)-D-ribofuranose
• CAS No.: 304436-74-6
• Molecular Formula: C₃₂H₃₀F₂O₄
• Molecular Weight: 516.585
• Mol file: 304436-74-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about 2',3',5'-tri-O-benzyl-1'-deoxy-β-1'-(2,4-difluorophenyl)-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:

(2S,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-2-(2,4-difluoro-phenyl)-tetrahydro-furan-2-ol → 2',3',5'-tri-O-benzyl-1'-deoxy-β-1'-(2,4-difluorophenyl)-D-ribofuranose (304436-74-6)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 1h;

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

Reference yield:

C32H30F2O5 (1067677-89-7) → 2',3',5'-tri-O-benzyl-1'-deoxy-β-1'-(2,4-difluorophenyl)-D-ribofuranose (304436-74-6)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 12h; stereoselective reaction;

DOI:10.1002/chem.200800837

Reference yield:

2,4-difluorobromobenzene (348-57-2) → 2',3',5'-tri-O-benzyl-1'-deoxy-β-1'-(2,4-difluorophenyl)-D-ribofuranose (304436-74-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / diethyl ether / -78 °C

1.2: diethyl ether

2.1: triethylsilane; BF₃*Et₂O

With triethylsilane; n-butyllithium; boron trifluoride diethyl etherate; In diethyl ether;

DOI:10.1081/NCN-200059755

upstream raw materials:

2,4-difluorobromobenzene

(3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one

C₃₂H₃₀F₂O₅

Downstream raw materials:

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

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

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