N-Monodemethyl-1-deoxypyrromycin

Base Information

• Chemical Name: N-Monodemethyl-1-deoxypyrromycin
• CAS No.: 65222-75-5
• Deprecated CAS: 67508-88-7
• Molecular Formula: C₂₉H₃₃NO₁₀
• Molecular Weight: 555.582
• DSSTox Substance ID: DTXSID30983832
• Nikkaji Number: J78.738H
• Wikidata: Q82970830
• Mol file: 65222-75-5.mol

Synonyms:N-Monodemethyl-1-deoxypyrromycin;65222-75-5;1-Naphthacenecarboxylic acid, 1,2,3,4,6,11-hexahydro-6,11-dioxo-2-ethyl-4-((2,3,6-trideoxy-3-amino-alpha-L-lyxo-hexopyranosyl)oxy)-2,5,7-trihydroxy-, methyl ester, (1R-(1-alpha,2-beta,4-beta))-;DTXSID30983832;Methyl 2-ethyl-2,5,7-trihydroxy-6,11-dioxo-4-{[2,3,6-trideoxy-3-(methylamino)hexopyranosyl]oxy}-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

Chemical Property of N-Monodemethyl-1-deoxypyrromycin

Chemical Property:

• Vapor Pressure: 1.05E-21mmHg at 25°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 6
• Exact Mass: 555.21044625
• Heavy Atom Count: 40
• Complexity: 992

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC1(CC(C2=C(C3=C(C=C2C1C(=O)OC)C(=O)C4=C(C3=O)C(=CC=C4)O)O)OC5CC(C(C(O5)C)O)NC)O
• Isomeric SMILES: CC[C@]1(C[C@@H](C2=C(C3=C(C=C2[C@H]1C(=O)OC)C(=O)C4=C(C3=O)C(=CC=C4)O)O)O[C@H]5C[C@@H]([C@@H]([C@@H](O5)C)O)NC)O

Technology Process of N-Monodemethyl-1-deoxypyrromycin

There total 23 articles about N-Monodemethyl-1-deoxypyrromycin 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:

(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) → N-demethylaklavin (65222-75-5,67508-88-7) + (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 (65222-75-5,67508-88-7)

Guidance literature:

With sodium methylate; In methanol; at -20 ℃; for 2h;

DOI:10.1021/ja00404a047

Reference yield:

(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) → N-demethylaklavin (65222-75-5,67508-88-7) + (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 (65222-75-5,67508-88-7)

Guidance literature:

With sodium methylate; In methanol; at -20 ℃; for 2h;

DOI:10.1021/ja00404a047

Reference yield:

9-epi-aklavinone 7-methyl ether (78773-17-8,78773-18-9,78773-19-0,78773-20-3) → N-demethylaklavin (65222-75-5,67508-88-7)

Guidance literature:

Multi-step reaction with 4 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

4: sodium methoxide / methanol / 2 h / -20 °C

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

DOI:10.1021/ja00404a047

upstream raw materials:

(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

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

9-epi-aklavinone 7-methyl ether

7-epi-aklavinone 7-methyl ether

Downstream raw materials:

aklavin