1,2-Di-O-acetyl-5-O-benzoyl-3-deoxy-3-fluoro-D-xylofuranose

Base Information

• Chemical Name: 1,2-Di-O-acetyl-5-O-benzoyl-3-deoxy-3-fluoro-D-xylofuranose
• CAS No.: 159099-24-8
• Molecular Formula: C₁₆H₁₇FO₇
• Molecular Weight: 340.305
• Mol file: 159099-24-8.mol

Synonyms:1,2-Di-O-acetyl-5-O-benzoyl-3-deoxy-3-fluoro-D-xylofuranose

Chemical Property of 1,2-Di-O-acetyl-5-O-benzoyl-3-deoxy-3-fluoro-D-xylofuranose

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-Di-O-acetyl-5-O-benzoyl-3-deoxy-3-fluoro-D-xylofuranose

There total 18 articles about 1,2-Di-O-acetyl-5-O-benzoyl-3-deoxy-3-fluoro-D-xylofuranose 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: 95.7%

acetic anhydride (108-24-7) + ((3aR,5R,6S,6aS)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate (125291-12-5) → (3S,4S,5R)-5-((benzoyloxy)methyl)-4-fluorotetrahydrofuran-2,3-diyl diacetate (159099-24-8)

Guidance literature:

With sulfuric acid; acetic acid; for 15h; Ambient temperature;

DOI:10.1016/0008-6215(94)84007-5

Reference yield: 47.0%

acetic anhydride (108-24-7) + ((3aR,5R,6S,6aS)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate (125291-12-5) → (3S,4S,5R)-5-((benzoyloxy)methyl)-4-fluorotetrahydrofuran-2,3-diyl diacetate (159099-24-8) + Benzoic acid (2R,3S,4S)-2,4,5,5-tetraacetoxy-3-fluoro-pentyl ester

Guidance literature:

With sulfuric acid; acetic acid;

DOI:10.1016/0008-6215(93)84056-C

Reference yield:

((3aR,5R,65,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate (6612-91-5) → (3S,4S,5R)-5-((benzoyloxy)methyl)-4-fluorotetrahydrofuran-2,3-diyl diacetate (159099-24-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / 4-(dimethylamino)pyridine, diethylaminosulfur trifluoride / CH₂Cl₂ / 18 h / -10 - 20 °C

2: 47 percent / CH₃COOH, H₂SO₄

With dmap; diethylamino-sulfur trifluoride; sulfuric acid; acetic acid; In dichloromethane;

DOI:10.1016/0008-6215(93)84056-C

upstream raw materials:

acetic anhydride

((3aR,5R,6S,6aS)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

(R)-1-((3aR,5R,6S,6aS)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol

(1,2:5,6)-di-O-isopropylidene-D-gulose

Downstream raw materials:

1-(3-deoxy-3-fluoro-β-D-lyxofuranosyl)thymine

3'-deoxy-3'-fluoro-5-methyl-1-β-D-xylofuranosyluracil

N2-acetyl-9-(5-O-benzoyl-2,3-dideoxy-3-fluoro-β-D-xylofuranosyl)guanine