1-O-acetyl-5-O-benzoyl-2,3-dideoxy-2,3-difluoro-α/β-D-arabinofuranoside

Base Information

• Chemical Name: 1-O-acetyl-5-O-benzoyl-2,3-dideoxy-2,3-difluoro-α/β-D-arabinofuranoside
• CAS No.: 1062520-03-9
• Molecular Formula: C₁₄H₁₄F₂O₅
• Molecular Weight: 300.259
• Mol file: 1062520-03-9.mol

Synonyms:1-O-acetyl-5-O-benzoyl-2,3-dideoxy-2,3-difluoro-α/β-D-arabinofuranoside

Chemical Property of 1-O-acetyl-5-O-benzoyl-2,3-dideoxy-2,3-difluoro-α/β-D-arabinofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-acetyl-5-O-benzoyl-2,3-dideoxy-2,3-difluoro-α/β-D-arabinofuranoside

There total 8 articles about 1-O-acetyl-5-O-benzoyl-2,3-dideoxy-2,3-difluoro-α/β-D-arabinofuranoside 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: 77.0%

acetic anhydride (108-24-7) + methyl 5-O-benzoyl-2,3-dideoxy-2,3-difluoro-α-D-arabinofuranoside (237410-14-9) → 1-O-acetyl-5-O-benzoyl-2,3-dideoxy-2,3-difluoro-α/β-D-arabinofuranoside (1062520-03-9)

Guidance literature:

With sulfuric acid; acetic acid; at 0 - 4 ℃; for 18.5h;

DOI:10.1080/15257770701534063

Reference yield: 77.0%

acetic anhydride (108-24-7) + methyl 5-O-benzoyl-2,3-dideoxy-2,3-difluoro-α-D-arabinofuranoside (237410-14-9) → 1-O-acetyl-5-O-benzoyl-2,3-dideoxy-2,3-difluoro-α/β-D-arabinofuranoside (1062520-03-9) + C17H20F2O7 + C17H20F2O7

Guidance literature:

With sulfuric acid; acetic acid; at 0 - 4 ℃; for 18h;

DOI:10.1515/hc-2015-0174

Reference yield:

methyl xylofuranoside (1824-96-0,1824-97-1,3795-68-4,3795-69-5,4229-54-3,5531-18-0,7473-45-2,13039-63-9,13039-64-0,13039-65-1,13039-67-3,22416-73-5,22861-09-2,25129-51-5,52485-92-4,52689-55-1,52689-56-2,56607-40-0,72880-70-7,79083-42-4,86782-30-1,86782-31-2,89615-03-2,89673-67-6,89707-99-3,102045-32-9,135910-17-7) → 1-O-acetyl-5-O-benzoyl-2,3-dideoxy-2,3-difluoro-α/β-D-arabinofuranoside (1062520-03-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: di(n-butyl)tin oxide / methanol / 1.25 h / 20 °C / Reflux

1.2: 5 h / 20 °C

2.1: diethylamino-sulfur trifluoride / dichloromethane / 10.5 h / 20 - 29 °C

3.1: acetic acid; sulfuric acid / 3.33 h / 0 - 25 °C

With diethylamino-sulfur trifluoride; sulfuric acid; di(n-butyl)tin oxide; acetic acid; In methanol; dichloromethane;

DOI:10.1016/j.tet.2019.02.027

upstream raw materials:

acetic anhydride

methyl 5-O-benzoyl-2,3-dideoxy-2,3-difluoro-α-D-arabinofuranoside

((2R,3S,4S,5S)-3-fluoro-4-hydroxy-5-methoxytetrahydrofuran-2-yl)methyl benzoate

methyl xylofuranoside

Downstream raw materials:

C₁₂H₁₁BrF₂O₃

5-O-benzoyl-2,3-dideoxy-2,3-difluoro-α-D-arabinofuranosyl bromide