4-Fluoro-4-deoxy-β-D-glucopyranose

Base Information

• Chemical Name: 4-Fluoro-4-deoxy-β-D-glucopyranose
• CAS No.: 27108-04-9
• Molecular Formula: C6H11FO5
• Molecular Weight: 182.15
• Hs Code.: 2932999099
• Mol file: 27108-04-9.mol

Synonyms:4-Deoxy-4-fluoro-β-D-glucopyranose

Chemical Property of 4-Fluoro-4-deoxy-β-D-glucopyranose

Chemical Property:

• Boiling Point: 370.1±42.0 °C(Predicted)
• PKA: 11.80±0.70(Predicted)
• PSA: 90.15000
• Density: 1.59±0.1 g/cm3(Predicted)
• LogP: -2.24420

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Fluoro-4-deoxy-β-D-glucopyranose

There total 5 articles about 4-Fluoro-4-deoxy-β-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:

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

Reference yield:

1,6-anhydro-4-O-(4-toluenesulfonyl)-β-D-glucopyranose (23643-29-0) → 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 3 steps

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

1.2: 2 h / 0 - 20 °C / Inert atmosphere

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

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

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

DOI:10.1002/chem.202002825

upstream raw materials:

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

levoglucosan

1,6-anhydro-4-O-(4-toluenesulfonyl)-β-D-glucopyranose

1,6:3,4-Dianhydro-2-O-benzyl-β-D-galactopyranose

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.