1,6-Anhydro-2,4-dideoxy-2,4-difluoro-β-D-glucopyranose

Base Information

• Chemical Name: 1,6-Anhydro-2,4-dideoxy-2,4-difluoro-β-D-glucopyranose
• CAS No.: 29332-85-2
• Molecular Formula: C6H8F2O3
• Molecular Weight: 166.1227264
• Mol file: 29332-85-2.mol

Synonyms:1,6-Anhydro-2,4-dideoxy-2,4-difluoro-β-D-glucopyranose

Chemical Property of 1,6-Anhydro-2,4-dideoxy-2,4-difluoro-β-D-glucopyranose

Chemical Property:

• Melting Point: 96 °C (acetone)
• PSA: 38.69000
• LogP: -0.22140

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-Anhydro-2,4-dideoxy-2,4-difluoro-β-D-glucopyranose

There total 10 articles about 1,6-Anhydro-2,4-dideoxy-2,4-difluoro-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: 60.0%

[(1R,2S,3S,4R,5R)-3-hydroxy-4-(p-tolylsulfonyl)-6,8-dioxabicyclo[3.2.1]oct-2-yl]-4-methylbenzenesulfonic acid (20204-80-2) → 1,6-anhydro-2,4-dideoxy-2,4-difluoro-β-D-glucopyranoside (29332-85-2)

Guidance literature:

With potassium hydrogen difluoride; tetrabutyl ammonium fluoride; at 180 ℃; for 24h; Inert atmosphere;

DOI:10.1021/acs.joc.9b00795

Reference yield: 54.0%

1,6:3,4-dianhydro-2-O-tosyl-D-galactose (6167-32-4) → 1,6-anhydro-2,4-dideoxy-2,4-difluoro-β-D-glucopyranoside (29332-85-2)

Guidance literature:

With potassium fluoride; potassium hydrogen bifluoride; In 1,2-dimethoxyethane; at 170 ℃; for 2h;

DOI:10.1021/acs.joc.9b00310

Reference yield: 22.0%

1,6:2,3-dianhydro-4-deoxy-4-fluoro-β-D-mannopyranose (33557-14-1) → 1,6-anhydro-2,4-dideoxy-2,4-difluoro-β-D-glucopyranoside (29332-85-2)

Guidance literature:

With potassium hydrogen fluoride; In ethylene glycol; at 0.2 ℃; for 3h; Inert atmosphere;

DOI:10.1002/chem.201901346

upstream raw materials:

1,6:3,4-dianhydro-2-O-tosyl-D-galactose

[(1R,2S,3S,4R,5R)-3-hydroxy-4-(p-tolylsulfonyl)-6,8-dioxabicyclo[3.2.1]oct-2-yl]-4-methylbenzenesulfonic acid

1,6:2,3-dianhydro-β-D-mannopyranose

1,6:2,3-dianhydro-4-O-(4-toluenesulfonyl)-β-D-mannopyranose

Downstream raw materials:

(1R,2S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,4-diol

Refernces

• 1、 Troup, Robert I.,Jeffries, Benjamin,Saudain, Raphael El-Bekri,Georgiou, Eleni,Fish, Johanna,Scott, James S.,Chiarparin, Elisabetta,Fallan, Charlene,Linclau, Bruno. "Skipped Fluorination Motifs: Synthesis of Building Blocks and Comparison of Lipophilicity Trends with Vicinal and Isolated Fluorination Motifs". . p. 1882 - 1900. Retrieved 2021/02/03.
• 2、 Denavit, Vincent,St-Gelais, Jacob,Tremblay, Thomas,Giguère, Denis. "Exploring the Chemistry of Non-sticky Sugars: Synthesis of Polyfluorinated Carbohydrate Analogues of d-Allopyranose". supporting information. p. 9272 - 9279. Retrieved 2019/07/05.