(1R,2R,4S)-2-Ethyl-2,5,7-trihydroxy-4-[(2R,4S,5S,6S)-6-methyl-4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-5-(4-nitro-benzoyloxy)-tetrahydro-pyran-2-yloxy]-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester

Base Information

• Chemical Name: (1R,2R,4S)-2-Ethyl-2,5,7-trihydroxy-4-[(2R,4S,5S,6S)-6-methyl-4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-5-(4-nitro-benzoyloxy)-tetrahydro-pyran-2-yloxy]-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester
• CAS No.: 78773-24-7
• Molecular Formula: C₃₈H₃₅F₃N₂O₁₄
• Molecular Weight: 800.696

Synonyms:

Chemical Property of (1R,2R,4S)-2-Ethyl-2,5,7-trihydroxy-4-[(2R,4S,5S,6S)-6-methyl-4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-5-(4-nitro-benzoyloxy)-tetrahydro-pyran-2-yloxy]-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (1R,2R,4S)-2-Ethyl-2,5,7-trihydroxy-4-[(2R,4S,5S,6S)-6-methyl-4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-5-(4-nitro-benzoyloxy)-tetrahydro-pyran-2-yloxy]-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester

There total 20 articles about (1R,2R,4S)-2-Ethyl-2,5,7-trihydroxy-4-[(2R,4S,5S,6S)-6-methyl-4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-5-(4-nitro-benzoyloxy)-tetrahydro-pyran-2-yloxy]-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl 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: 30.0%

4-Nitro-benzoic acid (2S,3S,4S)-2-methyl-4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-3,4-dihydro-2H-pyran-3-yl ester (78773-23-6) + (+/-)-aklavinone (78821-97-3) → (1S,2S,4R)-2-Ethyl-2,5,7-trihydroxy-4-[(2R,4S,5S,6S)-6-methyl-4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-5-(4-nitro-benzoyloxy)-tetrahydro-pyran-2-yloxy]-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester (78773-24-7,78822-00-1) + (1R,2R,4S)-2-Ethyl-2,5,7-trihydroxy-4-[(2R,4S,5S,6S)-6-methyl-4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-5-(4-nitro-benzoyloxy)-tetrahydro-pyran-2-yloxy]-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester (78773-24-7,78822-00-1)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; at 50 ℃;

DOI:10.1021/ja00404a047

Reference yield: 30.0%

4-Nitro-benzoic acid (2S,3S,4S)-2-methyl-4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-3,4-dihydro-2H-pyran-3-yl ester (78773-23-6) + (+/-)-aklavinone (78821-97-3) → (1S,2S,4R)-2-Ethyl-2,5,7-trihydroxy-4-[(2R,4S,5S,6S)-6-methyl-4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-5-(4-nitro-benzoyloxy)-tetrahydro-pyran-2-yloxy]-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester (78773-24-7,78822-00-1) + (1R,2R,4S)-2-Ethyl-2,5,7-trihydroxy-4-[(2R,4S,5S,6S)-6-methyl-4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-5-(4-nitro-benzoyloxy)-tetrahydro-pyran-2-yloxy]-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester (78773-24-7,78822-00-1)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; at 50 ℃;

DOI:10.1021/ja00404a047

Reference yield:

9-epi-aklavinone 7-methyl ether (78773-17-8,78773-18-9,78773-19-0,78773-20-3) → (1S,2S,4R)-2-Ethyl-2,5,7-trihydroxy-4-[(2R,4S,5S,6S)-6-methyl-4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-5-(4-nitro-benzoyloxy)-tetrahydro-pyran-2-yloxy]-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester (78773-24-7,78822-00-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 11 percent / potassium carbonate / methanol / 1.75 h / 65 °C

2: trifluoroacetic acid / Ambient temperature

3: 30 percent / p-toluenesulfonic acid monohydrate / benzene / 50 °C

With potassium carbonate; toluene-4-sulfonic acid; trifluoroacetic acid; In methanol; benzene;

DOI:10.1021/ja00404a047

upstream raw materials:

4-Nitro-benzoic acid (2S,3S,4S)-2-methyl-4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-3,4-dihydro-2H-pyran-3-yl ester

(+/-)-aklavinone

(2S,3S,4S)-2-methyl-3-(4-nitrobenzoyloxy)-4-trifluoracetamido-3,4-dihydro-2H-pyran

4-nitro-benzoyl chloride

Downstream raw materials:

(+)-aklavinone

N-demethylaklavin

(1S,2R,4S)-2-Ethyl-2,5,7-trihydroxy-4-((2R,4S,5S,6S)-5-hydroxy-6-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester

aklavin

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