4-Deoxy-4-fluoro-beta-d-glucopyranose

Base Information

• Chemical Name: 4-Deoxy-4-fluoro-beta-d-glucopyranose
• CAS No.: 62182-11-0
• Molecular Formula: C₆H₁₁FO₅
• Molecular Weight: 182.149
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID40977762
• Nikkaji Number: J37.021E
• Wikidata: Q82963057
• Mol file: 62182-11-0.mol

Synonyms:4-deoxy-4-fluoro-beta-D-glucopyranose

Chemical Property of 4-Deoxy-4-fluoro-beta-d-glucopyranose

Chemical Property:

• Vapor Pressure: 5.52E-07mmHg at 25°C
• Refractive Index: 1.535
• Boiling Point: 370.1 °C at 760 mmHg
• Flash Point: 170.1 °C
• PSA: 90.15000
• Density: 1.59 g/cm³
• LogP: -2.24420
• Storage Temp.: 2-8°C
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 182.05905161
• Heavy Atom Count: 12
• Complexity: 155

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 4-Deoxy-4-fluoro-beta-d-glucopyranose

There total 7 articles about 4-Deoxy-4-fluoro-beta-d-glucopyranose 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:

1,6-anhydro-2-O-benzyl-4-deoxy-4-fluoro-β-D-glucopyranose → 4-deoxy-4-fluoro-β-D-glucopyranose (27108-04-9) + 3-fluoro-3-deoxy-α-D-glucose (62182-11-0)

Guidance literature:

With boron trichloride; In dichloromethane; at 0 - 20 ℃; for 2h; Overall yield = 85 percent; Overall yield = 18.7 mg; Inert atmosphere;

DOI:10.1002/chem.202002825

Reference yield:

methyl 2,3,6-tri-O-benzoyl-α-D-galactopyranoside (3601-36-3,6344-46-3) → 3-fluoro-3-deoxy-α-D-glucose (62182-11-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 56 percent / diethylaminosulfur trifluoride, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1) -20 deg C, 15 min, 2) RT, 24 h

2: 78 percent / 1M NaOMe in MeOH / 18 h / Ambient temperature

3: H₂O, Dowex 50W-X₈(1+)> / 25 h / Heating

With dmap; diethylamino-sulfur trifluoride; Dowex 50W-X8; water; sodium methylate; In dichloromethane;

DOI:10.1016/S0008-6215(00)90028-4

Reference yield:

levoglucosan (498-07-7) → 4-deoxy-4-fluoro-β-D-glucopyranose (27108-04-9) + 3-fluoro-3-deoxy-α-D-glucose (62182-11-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine / toluene / 23 h / 0 - 20 °C / Inert atmosphere

2.1: sodium methylate / dichloromethane; methanol / 2 h / 0 - 20 °C / Inert atmosphere

2.2: 2 h / 0 - 20 °C / Inert atmosphere

3.1: tetra-n-butylammoniumfluoride trihydrate; potassium hydrogen bifluoride / 3 h / 180 °C / Inert atmosphere

4.1: boron trichloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

With pyridine; potassium hydrogen bifluoride; sodium methylate; boron trichloride; tetra-n-butylammoniumfluoride trihydrate; In methanol; dichloromethane; toluene;

DOI:10.1002/chem.202002825

upstream raw materials:

Methyl 4-Deoxy-4-fluoro-α-D-glucopyranoside

methyl 2,3,6-tri-O-benzoyl-α-D-galactopyranoside

methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-fluoro-α-D-glucopyranoside

levoglucosan

Refernces

• 1、 Withers, Stephen G.,MacLennan, David J.,Street, Ian P.. "THE SYNTHESIS AND HYDROLYSIS OF A SERIES OF DEOXYFLUORO-D-GLUCOPYRANOSYL PHOSPHATES". . p. 127 - 144. Retrieved 2007/10/02.