9-acetyl-7-tert-butoxy-6,9,11-trihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione

Base Information

• Chemical Name: 9-acetyl-7-tert-butoxy-6,9,11-trihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione
• CAS No.: 91281-71-9
• Molecular Formula: C₂₄H₂₄O₇
• Molecular Weight: 424.45
• Mol file: 91281-71-9.mol

Synonyms:(7R,9R)-9-Acetyl-7-tert-butoxy-6,9,11-trihydroxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione;4-Demethoxy-7-O-tert-butyldaunomycinone;

Chemical Property of 9-acetyl-7-tert-butoxy-6,9,11-trihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione

Chemical Property:

• Melting Point: 217 - 220 °C
• PSA: 121.13000
• LogP: 2.99570

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-acetyl-7-tert-butoxy-6,9,11-trihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione

There total 12 articles about 9-acetyl-7-tert-butoxy-6,9,11-trihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione 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: 91.0%

cis-(+/-)-9-(2-trimethylsilylethynyl)-7,8,9,10-tetrahdyro-7-(1,1-dimethylethoxy)-6,9,11-trihydroxy-5,12-naphthacenedione → cis-(+/-)-9-acetyl-7,8,9,10-tetrahydro-7-(1,1-dimethylethoxy)-6,9,11-trihydroxy-5,12-naphthacenedione (91281-71-9)

Guidance literature:

With sulfuric acid; mercury(II) oxide; In tetrahydrofuran; for 24h; Ambient temperature;

DOI:10.1016/S0040-4020(01)80160-5

Reference yield: 85.0%

1,2,3,4-Tetrahydro-1-tert-butoxy-3-ethynyl-3,5,12-trihydroxynaphthacene-6,11-dione (91281-70-8) → cis-(+/-)-9-acetyl-7,8,9,10-tetrahydro-7-(1,1-dimethylethoxy)-6,9,11-trihydroxy-5,12-naphthacenedione (91281-71-9)

Guidance literature:

With sulfuric acid; mercury(II) oxide; In water; acetone; at 60 ℃; for 0.166667h;

DOI:10.1021/jo00193a034

Reference yield:

3-[(1,1-dimethylethyl)oxy]cyclobutanone (30830-28-5) → cis-(+/-)-9-acetyl-7,8,9,10-tetrahydro-7-(1,1-dimethylethoxy)-6,9,11-trihydroxy-5,12-naphthacenedione (91281-71-9)

Guidance literature:

Multi-step reaction with 6 steps

1: triethylamine / acetonitrile / 50 °C

2: 86 percent

3: 84 percent / tetrahydrofuran / 2 h / Ambient temperature

4: Zn/acetic acid / 24 h

5: Mg, ethyl bromide; O₂/0.5percent NaOH

6: 85 percent / HgO, conc. H₂SO₄ / acetone; H₂O / 0.17 h / 60 °C

With sodium hydroxide; ethyl bromide; sulfuric acid; oxygen; magnesium; acetic acid; triethylamine; mercury(II) oxide; zinc; In tetrahydrofuran; water; acetone; acetonitrile;

DOI:10.1021/jo00193a034

upstream raw materials:

1,2,3,4-Tetrahydro-1-tert-butoxy-3-ethynyl-3,5,12-trihydroxynaphthacene-6,11-dione

1,4,9,10-tetrahydro-5,8-dihydroxy-9,10-dioxo-1,4-ethanoanthracene

1,4,6,6a,7,8,9,10,10a,11-decahydro-5,12-dihydroxy-7-(1,1-dimethylethoxy)-1,4-ethanonaphthacene-6,9,11(10H)-trione

3-[(1,1-dimethylethyl)oxy]cyclobutanone

Refernces

• 1、 Potman,Janssen,Scheeren,Nivard. "Application of 1-tert-butoxy-3-[(trimethylsilyl)oxy]buta-1,3-diene in the preparation of functionalized β-hydroxycyclohexanone derivatives, including valuable precursors of daunomycinone analogues". . p. 3628 - 3634. Retrieved 2007/10/02.