Benzoic acid (2R,3R,4R)-4,5-diacetoxy-2-(2-acetoxy-ethyl)-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3R,4R)-4,5-diacetoxy-2-(2-acetoxy-ethyl)-tetrahydro-furan-3-yl ester
• CAS No.: 620169-18-8
• Molecular Formula: C₁₉H₂₂O₉
• Molecular Weight: 394.378

Synonyms:Benzoic acid (2R,3R,4R)-4,5-diacetoxy-2-(2-acetoxy-ethyl)-tetrahydro-furan-3-yl ester

Chemical Property of Benzoic acid (2R,3R,4R)-4,5-diacetoxy-2-(2-acetoxy-ethyl)-tetrahydro-furan-3-yl ester

Chemical Property:

Purity/Quality:

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Technology Process of Benzoic acid (2R,3R,4R)-4,5-diacetoxy-2-(2-acetoxy-ethyl)-tetrahydro-furan-3-yl ester

There total 7 articles about Benzoic acid (2R,3R,4R)-4,5-diacetoxy-2-(2-acetoxy-ethyl)-tetrahydro-furan-3-yl ester 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: 68.0%

acetic anhydride (108-24-7) + 3-O-benzoyloxy-5-deoxy-1,2-O-isopropylidene-α-D-ribohexofuranose (113808-25-6) → Benzoic acid (2R,3R,4R)-4,5-diacetoxy-2-(2-acetoxy-ethyl)-tetrahydro-furan-3-yl ester (620169-18-8)

Guidance literature:

With sulfuric acid; acetic acid; at 20 ℃; for 20h;

DOI:10.1021/ja0360900

Reference yield:

benzoyl chloride (98-88-4) → Benzoic acid (2R,3R,4R)-4,5-diacetoxy-2-(2-acetoxy-ethyl)-tetrahydro-furan-3-yl ester (620169-18-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridine / CH₂Cl₂ / 1 h / 0 °C

2.1: aq. AcOH / 24 h / 20 °C

3.1: NaI

4.1: BH₃*Me₂S

4.2: 68 percent / NaHCO₃; aq. H₂O₂

5.1: 68 percent / H₂SO₄; AcOH / 20 h / 20 °C

With pyridine; dimethylsulfide borane complex; sulfuric acid; acetic acid; sodium iodide; In dichloromethane;

DOI:10.1021/ja0360900

Reference yield:

Diacetone D-glucose (2595-05-3) → Benzoic acid (2R,3R,4R)-4,5-diacetoxy-2-(2-acetoxy-ethyl)-tetrahydro-furan-3-yl ester (620169-18-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridine / CH₂Cl₂ / 1 h / 0 °C

2.1: aq. AcOH / 24 h / 20 °C

3.1: NaI

4.1: BH₃*Me₂S

4.2: 68 percent / NaHCO₃; aq. H₂O₂

5.1: 68 percent / H₂SO₄; AcOH / 20 h / 20 °C

With pyridine; dimethylsulfide borane complex; sulfuric acid; acetic acid; sodium iodide; In dichloromethane;

DOI:10.1021/ja0360900

upstream raw materials:

acetic anhydride

3-O-benzoyloxy-5-deoxy-1,2-O-isopropylidene-α-D-ribohexofuranose

Benzoic acid (3aR,5R,6R,6aR)-2,2-dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

(+)-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-yl benzoate

Downstream raw materials:

1-(2,6-diacetyl-3-O-benzoyl-5-deoxy-β-D-ribo-hexofuranosyl)uracil

C₂₄H₂₂N₂O₈

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