4-deoxy-4-fluoro-α-D-glucopyranosyl

Base Information

• Chemical Name: 4-deoxy-4-fluoro-α-D-glucopyranosyl
• CAS No.: 109923-29-7
• Molecular Formula: C₆H₁₂FO₈P*2C₆H₁₃N
• Molecular Weight: 460.48
• Mol file: 109923-29-7.mol

Synonyms:

Chemical Property of 4-deoxy-4-fluoro-α-D-glucopyranosyl

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-deoxy-4-fluoro-α-D-glucopyranosyl

There total 4 articles about 4-deoxy-4-fluoro-α-D-glucopyranosyl 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-deoxy-4-fluoro-D-galactose (238418-56-9) → 4-deoxy-4-fluoro-α-D-glucopyranosyl (109923-29-7)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOAc / 1.) reflux, 50 min, 2.) r.t., 2 h

2: 1.) H₃PO₄, LiOH / 1.) 55 deg C, 2.5 h; r.t., overnight, 2.) H₂O

With lithium hydroxide; phosphoric acid; sodium acetate;

DOI:10.1021/jo00102a024

Reference yield:

1,2,3,6-tetra-O-acetyl-4-deoxy-4-fluoro-α-D-galactopyranoside (40010-22-8) + cyclohexylamine (108-91-8,157973-60-9) → 4-deoxy-4-fluoro-α-D-glucopyranosyl (109923-29-7) + 4-Deoxy-4-fluoro-β-D-glucopyranosyl

Guidance literature:

With lithium hydroxide; phosphoric acid; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) 55 deg C, 2.5 h; r.t., overnight, 2.) H₂O;

DOI:10.1021/jo00102a024

Reference yield:

(3R,4R,5S,6R)-5-fluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4-triol (30694-44-1) → 4-deoxy-4-fluoro-α-D-glucopyranosyl (109923-29-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / pyridine / 48 h / Ambient temperature

2: 1) phosphoric acid, 2) Dowex 50W-X₈(1+)> / 1) 55 deg C, 2.5 h

With pyridine; phosphoric acid; Dowex 50W-X8;

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

upstream raw materials:

(2S,3R,4R,5R,6R)-6-(acetoxymethyl)-5-fluorotetrahydro-2H-pyran-2,3,4-triyl triacetate

cyclohexylamine

1,2,3,6-tetra-O-acetyl-4-deoxy-4-fluoro-α-D-galactopyranoside

4-deoxy-4-fluoro-D-galactose

Downstream raw materials:

(3R,4R,5S,6R)-5-fluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4-triol