4-(3,5-di-O-benzoyl-1,4-anhydro-2-deoxy-D-erythro-pent-1-enofuranosyl)-4-oxo-2-butenoic acid

Base Information

• Chemical Name: 4-(3,5-di-O-benzoyl-1,4-anhydro-2-deoxy-D-erythro-pent-1-enofuranosyl)-4-oxo-2-butenoic acid
• CAS No.: 109930-06-5
• Molecular Formula: C₂₃H₁₈O₈
• Molecular Weight: 422.391

Synonyms:4-(3,5-di-O-benzoyl-1,4-anhydro-2-deoxy-D-erythro-pent-1-enofuranosyl)-4-oxo-2-butenoic acid

Chemical Property of 4-(3,5-di-O-benzoyl-1,4-anhydro-2-deoxy-D-erythro-pent-1-enofuranosyl)-4-oxo-2-butenoic acid

Chemical Property:

Purity/Quality:

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Technology Process of 4-(3,5-di-O-benzoyl-1,4-anhydro-2-deoxy-D-erythro-pent-1-enofuranosyl)-4-oxo-2-butenoic acid

There total 2 articles about 4-(3,5-di-O-benzoyl-1,4-anhydro-2-deoxy-D-erythro-pent-1-enofuranosyl)-4-oxo-2-butenoic 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: 80.6%

5-hydroxy-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranozyl)-furan-2(5H)-one (139236-90-1) → 4-(3,5-di-O-benzoyl-1,4-anhydro-2-deoxy-D-erythro-pent-1-enofuranosyl)-4-oxo-2-butenoic acid (109930-06-5)

Guidance literature:

With triethylamine; In benzene; for 4h; Ambient temperature;

DOI:10.1021/jo00229a017

Reference yield:

2-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)furan (86528-49-6) → 4-(3,5-di-O-benzoyl-1,4-anhydro-2-deoxy-D-erythro-pent-1-enofuranosyl)-4-oxo-2-butenoic acid (109930-06-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / chromium trioxide, conc. H₂SO₄ / H₂O; acetone / 4 h / Ambient temperature

2: 80.6 percent / triethylamine / benzene / 4 h / Ambient temperature

With chromium(VI) oxide; sulfuric acid; triethylamine; In water; acetone; benzene;

DOI:10.1021/jo00229a017

Reference yield: 22.0%

4-(3,5-di-O-benzoyl-1,4-anhydro-2-deoxy-D-erythro-pent-1-enofuranosyl)-4-oxo-2-butenoic acid (109930-06-5) → 4-(3,5-di-O-benzoyl-2-deoxy-β-D-erythro-pentofuranosyl)-4-oxobutyric acid (128745-68-6) + 4-(3,5-di-O-benzoyl-2-deoxy-α-D-erythro-pentofuranosyl)-4-oxobutyric acid (128745-69-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; for 12h; under 760 Torr;

upstream raw materials:

5-hydroxy-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranozyl)-furan-2(5H)-one

2-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)furan

Downstream raw materials:

4-(3,5-di-O-benzoyl-2-deoxy-β-D-erythro-pentofuranosyl)-4-oxobutyric acid

4-(3,5-di-O-benzoyl-2-deoxy-α-D-erythro-pentofuranosyl)-4-oxobutyric acid

3-(3,5-di-O-benzoyl-2-deoxy-β-D-erythro-pentofuranosyl)-4,5-dihydropyridazin-6(1H)-one

3-(3,5-di-O-benzoyl-2-deoxy-α-D-erythro-pentofuranosyl)-4,5-dihydropyridazin-6(1H)-one

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