(8S-cis)-8-Acetyl-10-[[(1,1-diMethylethyl)diMethylsilyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-Methoxy-5,12-naphthacenedione

Base Information

• Chemical Name: (8S-cis)-8-Acetyl-10-[[(1,1-diMethylethyl)diMethylsilyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-Methoxy-5,12-naphthacenedione
• CAS No.: 111248-01-2
• Molecular Formula: C₂₇H₃₂O₈Si
• Molecular Weight: 512.632
• Mol file: 111248-01-2.mol

Synonyms:

Chemical Property of (8S-cis)-8-Acetyl-10-[[(1,1-diMethylethyl)diMethylsilyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-Methoxy-5,12-naphthacenedione

Chemical Property:

• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)

Purity/Quality:

>95% ^*data from raw suppliers

(8S-cis)-8-Acetyl-10-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (8S-cis)-8-Acetyl-10-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione is an tert-butyldiphenylsilyl protected degredation product of Doxorubicin (D194500), an anthracycline antibiotic related to

Technology Process of (8S-cis)-8-Acetyl-10-[[(1,1-diMethylethyl)diMethylsilyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-Methoxy-5,12-naphthacenedione

There total 1 articles about (8S-cis)-8-Acetyl-10-[[(1,1-diMethylethyl)diMethylsilyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-Methoxy-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: 98.0%

(+)-Daunomycinone (21794-55-8) + 2,4-pentane dione t butyl dimethyl silyl enol ether (69404-97-3) → (2S,4S)-2-acetyl-4-tert-butyldimethylsilyloxy-2,5,12-trihydroxy-7-methoxy-1,2,3,4-tetrahydro-6,11-naphthacenedione (111248-01-2)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; for 2h; Ambient temperature;

DOI:10.1248/cpb.34.4613

Reference yield:

(2S,4S)-2-acetyl-4-tert-butyldimethylsilyloxy-2,5,12-trihydroxy-7-methoxy-1,2,3,4-tetrahydro-6,11-naphthacenedione (111248-01-2) → (+)-13-methyl-13-dihydrodaunorubicin hydrochloride (111248-05-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 69 percent / tetrahydrofuran; diethyl ether / 1.75 h / -20 °C

3: 63 percent / 0.1 M sodium hydroxide / tetrahydrofuran / 0.33 h / Ambient temperature

With sodium hydroxide; In tetrahydrofuran; diethyl ether;

DOI:10.1248/cpb.34.4613

upstream raw materials:

(+)-Daunomycinone

2,4-pentane dione t butyl dimethyl silyl enol ether

Downstream raw materials:

(+)-13-methyl-13-dihydrodaunorubicin hydrochloride