3-Deoxy-3-fluorosucrose

Base Information

• Chemical Name: 3-Deoxy-3-fluorosucrose
• CAS No.: 102039-76-9
• Molecular Formula: C₁₂H₂₁FO₁₀
• Molecular Weight: 344.291
• DSSTox Substance ID: DTXSID40907009
• Wikidata: Q82875877
• Mol file: 102039-76-9.mol

Synonyms:3-deoxy-3-fluorosucrose

Chemical Property of 3-Deoxy-3-fluorosucrose

Chemical Property:

• Vapor Pressure: 1.96E-22mmHg at 25°C
• Boiling Point: 696.4°Cat760mmHg
• Flash Point: 281.3°C
• PSA: 169.30000
• Density: 1.71g/cm³
• LogP: -4.41840
• XLogP3: -2.7
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 5
• Exact Mass: 344.11187502
• Heavy Atom Count: 23
• Complexity: 400

Purity/Quality:

99% ^*data from raw suppliers

3-Deoxy-3-fluorosucrose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(C(O1)OC2(C(C(C(O2)CO)O)O)CO)O)F)O)O
• Isomeric SMILES: C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)CO)O)O)CO)O)F)O)O

Technology Process of 3-Deoxy-3-fluorosucrose

There total 7 articles about 3-Deoxy-3-fluorosucrose 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:

4,6-O-isopropylidene sucrose hexabenzoate (60825-19-6) → 3-deoxy-3-fluorosucrose (102039-76-9)

Guidance literature:

Multi-step reaction with 7 steps

2: imidazole / dimethylformamide / 60 °C

3: 86 percent / LiAlH₄ / tetrahydrofuran / 3 h / 25 °C

4: chromium trioxide, pyridine, acetic anhydride / CH₂Cl₂ / 0.33 h / 25 °C

5: sodium borohydride / methanol / 0.5 h / 25 °C

6: 25 percent / diethylaminosulfur trifluoride / pyridine / 1 h / 25 °C

7: 1.) tetrabutylammonium chloride, potassium fluoride dihydrate; 2.) acetic acid / 1.) acetonitrile, 70 deg C, 3 d, 2.) THF, water, 18 h, 25 deg C

With pyridine; 1H-imidazole; chromium(VI) oxide; potassium fluoride; sodium tetrahydroborate; lithium aluminium tetrahydride; diethylamino-sulfur trifluoride; tetrabutyl-ammonium chloride; acetic anhydride; acetic acid; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(86)85014-5

Reference yield:

3-O-benzoyl-1',2:4,6-di-O-isopropylidenesucrose → 3-deoxy-3-fluorosucrose (102039-76-9)

Guidance literature:

Multi-step reaction with 6 steps

1: imidazole / dimethylformamide / 60 °C

2: 86 percent / LiAlH₄ / tetrahydrofuran / 3 h / 25 °C

3: chromium trioxide, pyridine, acetic anhydride / CH₂Cl₂ / 0.33 h / 25 °C

4: sodium borohydride / methanol / 0.5 h / 25 °C

5: 25 percent / diethylaminosulfur trifluoride / pyridine / 1 h / 25 °C

6: 1.) tetrabutylammonium chloride, potassium fluoride dihydrate; 2.) acetic acid / 1.) acetonitrile, 70 deg C, 3 d, 2.) THF, water, 18 h, 25 deg C

With pyridine; 1H-imidazole; chromium(VI) oxide; potassium fluoride; sodium tetrahydroborate; lithium aluminium tetrahydride; diethylamino-sulfur trifluoride; tetrabutyl-ammonium chloride; acetic anhydride; acetic acid; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(86)85014-5

Reference yield:

C36H70O11Si3 → 3-deoxy-3-fluorosucrose (102039-76-9)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium borohydride / methanol / 0.5 h / 25 °C

2: 25 percent / diethylaminosulfur trifluoride / pyridine / 1 h / 25 °C

3: 1.) tetrabutylammonium chloride, potassium fluoride dihydrate; 2.) acetic acid / 1.) acetonitrile, 70 deg C, 3 d, 2.) THF, water, 18 h, 25 deg C

With potassium fluoride; sodium tetrahydroborate; diethylamino-sulfur trifluoride; tetrabutyl-ammonium chloride; acetic acid; In pyridine; methanol;

DOI:10.1016/0008-6215(86)85014-5

upstream raw materials:

3',4',6'-tri-O-tert-butyldimethylsilyl-3-deoxy-3-fluoro-1',2:4,6-di-O-isopropylidenesucrose

4,6-O-isopropylidene sucrose hexabenzoate

3',4',6'-tri-O-tert-butyldimethylsilyl-1',2:4,6-di-O-isopropylideneallosucrose

3’,4’,6’-tris-O-tert-butyldimethylsilyl-1’,2:4,6-di-O-isopropylidene sucrose