digitoxigenin 4-O-acetyl-2,6-dideoxy-3-O-(p-methoxybenzoyl)-α-D-ribo-hexopyranoside

Base Information

• Chemical Name: digitoxigenin 4-O-acetyl-2,6-dideoxy-3-O-(p-methoxybenzoyl)-α-D-ribo-hexopyranoside
• CAS No.: 1345697-32-6
• Molecular Formula: C₃₉H₅₂O₁₀
• Molecular Weight: 680.836

Synonyms:digitoxigenin 4-O-acetyl-2,6-dideoxy-3-O-(p-methoxybenzoyl)-α-D-ribo-hexopyranoside

Chemical Property of digitoxigenin 4-O-acetyl-2,6-dideoxy-3-O-(p-methoxybenzoyl)-α-D-ribo-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of digitoxigenin 4-O-acetyl-2,6-dideoxy-3-O-(p-methoxybenzoyl)-α-D-ribo-hexopyranoside

There total 12 articles about digitoxigenin 4-O-acetyl-2,6-dideoxy-3-O-(p-methoxybenzoyl)-α-D-ribo-hexopyranoside 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: 66.0%

4-O-acetyl-2,6-dideoxy-3-O-(p-methoxybenzoyl)-β-D-ribo-hexopyranosyl o-(cyclopropylethynyl)benzoate (1345697-25-7) + (+)-digitoxigenin (143-62-4) → digitoxigenin 4-O-acetyl-2,6-dideoxy-3-O-(p-methoxybenzoyl)-β-D-ribo-hexopyranoside (1345697-30-4) + digitoxigenin 4-O-acetyl-2,6-dideoxy-3-O-(p-methoxybenzoyl)-α-D-ribo-hexopyranoside (1345697-32-6)

Guidance literature:

With triphenylphosphinegold(I) triflate; In dichloromethane; toluene; at 20 ℃; for 3h; Molecular sieve;

DOI:10.1021/jo201850z

Reference yield:

methyl 4,6-di-O-benzylidene-2,3-di-O-tosyl-α-D-glucopyranoside (65556-00-5) → digitoxigenin 4-O-acetyl-2,6-dideoxy-3-O-(p-methoxybenzoyl)-β-D-ribo-hexopyranoside (1345697-30-4) + digitoxigenin 4-O-acetyl-2,6-dideoxy-3-O-(p-methoxybenzoyl)-α-D-ribo-hexopyranoside (1345697-32-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium methylate / methanol; dichloromethane / 20 °C

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 50 °C

3.1: pyridine; dmap / toluene / 6 h / 100 °C

4.1: toluene-4-sulfonic acid / methanol / 2 h / 20 °C / pH 3

5.1: 1H-imidazole; iodine; triphenylphosphine / toluene / 1 h / 70 °C / Inert atmosphere

5.2: 1 h / 100 °C / Inert atmosphere

5.3: 5 h / 100 °C / Inert atmosphere

6.1: water; acetic acid / 4 h / 100 °C

7.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

8.1: triphenylphosphinegold(I) triflate / dichloromethane; toluene / 3 h / 20 °C / Molecular sieve

With pyridine; 1H-imidazole; dmap; lithium aluminium tetrahydride; triphenylphosphinegold(I) triflate; water; iodine; sodium methylate; toluene-4-sulfonic acid; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1021/jo201850z

Reference yield:

digitoxigen O-[2'',6''-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-O-[3'-O-acetyl-2',6'-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-(3-O-acetyl-2,6-dideoxy-β-D-ribo-hexopyranoside (57292-22-5) → digitoxigenin 4-O-acetyl-2,6-dideoxy-3-O-(p-methoxybenzoyl)-β-D-ribo-hexopyranoside (1345697-30-4) + digitoxigenin 4-O-acetyl-2,6-dideoxy-3-O-(p-methoxybenzoyl)-α-D-ribo-hexopyranoside (1345697-32-6)

Guidance literature:

Multi-step reaction with 3 steps

1: water; lithium hydroxide / methanol / 3 h / 20 °C

2: sulfuric acid / methanol / 5 h / 0 °C

3: triphenylphosphinegold(I) triflate / dichloromethane; toluene / 3 h / 20 °C / Molecular sieve

With triphenylphosphinegold(I) triflate; sulfuric acid; water; lithium hydroxide; In methanol; dichloromethane; toluene;

DOI:10.1021/jo201850z

upstream raw materials:

methyl 4,6-di-O-benzylidene-2,3-di-O-tosyl-α-D-glucopyranoside

digitoxigen O-[2'',6''-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-O-[3'-O-acetyl-2',6'-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-(3-O-acetyl-2,6-dideoxy-β-D-ribo-hexopyranoside

methyl 2-deoxy-3-O-(p-methoxybenzoyl)-α-D-ribo-hexopyranoside

methyl 4-O-acetyl-2,6-dideoxy-3-O-(p-methoxybenzoyl)-α-D-ribo-hexopyranoside

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