2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-arabino- and D-ribo-hexonic acid

Base Information

• Chemical Name: 2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-arabino- and D-ribo-hexonic acid
• CAS No.: 675124-51-3
• Molecular Formula: C₂₀H₁₈O₇
• Molecular Weight: 370.359
• Mol file: 675124-51-3.mol

Synonyms:2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-arabino- and D-ribo-hexonic acid

Chemical Property of 2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-arabino- and D-ribo-hexonic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-arabino- and D-ribo-hexonic acid

There total 4 articles about 2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-arabino- and D-ribo-hexonic acid 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: 83.0%

4S-benzoyloxy-5R-benzoyloxymethyltetrahydrofuran-2R/S-carbonitrile (675124-49-9) → 2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-arabino- and D-ribo-hexonic acid (675124-51-3)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 80 - 82 ℃; for 3.5h;

Reference yield:

((2R,3S)-3-(benzoyloxy)-5-methoxytetrahydrofuran-2-yl)methyl benzoate (108647-88-7) → 2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-arabino- and D-ribo-hexonic acid (675124-51-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / BF₃*OEt₂ / CH₂Cl₂ / 1.5 h / 0 °C

2: 72 percent / hydrochloric acid / dioxane / 6 h / 80 °C

With hydrogenchloride; boron trifluoride diethyl etherate; In 1,4-dioxane; dichloromethane;

DOI:10.1016/j.tet.2003.11.055

Reference yield:

1,3,5-tri-O-benzoyl-2-deoxy-D-ribofuranose (145416-96-2) → 2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-arabino- and D-ribo-hexonic acid (675124-51-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / BF₃*OEt₂ / CH₂Cl₂ / 1.5 h / 0 °C

2: 83 percent / conc. HCl / dioxane / 3.5 h / 80 - 82 °C

With hydrogenchloride; boron trifluoride diethyl etherate; In 1,4-dioxane; dichloromethane;

upstream raw materials:

4S-benzoyloxy-5R-benzoyloxymethyltetrahydrofuran-2R/S-carbonitrile

((2R,3S)-3-(benzoyloxy)-5-methoxytetrahydrofuran-2-yl)methyl benzoate

1,3,5-tri-O-benzoyl-2-deoxy-D-ribofuranose

D-2-deoxyribose

Downstream raw materials:

N-<1-(3-amino-4,5-dihydro-5-oxo-1,2,4-triazin-6-yl)ethyl>-2,5-anhydro-4,6-di-O-benzoyl-D-arabino-and-D-ribo-hexonamide

2-amino-7-(3',5'-di-O-benzoyl-2'-deoxy-β-D-erythro-pentofuranosyl)-3,4-dihydroimidazo<5,1-f><1,2,4>triazin-4-one

2-amino-7-(3',5'-di-O-benzoyl-2'-deoxy-α-D-erythro-pentofuranosyl)-3,4-dihydroimidazo<5,1-f><1,2,4>triazin-4-one

2-amino-7-(3',5'-di-O-benzoyl-2'-deoxy-β-D-erythro-pentofuranosyl)-3,4-dihydro-5-methylimidazo<5,1-f><1,2,4>triazin-4-one