7-O-ribofuranosyldaunomycinone

Base Information

• Chemical Name: 7-O-ribofuranosyldaunomycinone
• CAS No.: 105444-04-0
• Molecular Formula: C₂₆H₂₆O₁₂
• Molecular Weight: 530.485
• Mol file: 105444-04-0.mol

Synonyms:(8S,10S)-8-Acetyl-10-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yloxy)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione;

Chemical Property of 7-O-ribofuranosyldaunomycinone

Chemical Property:

• Vapor Pressure: 7.04E-29mmHg at 25°C
• Boiling Point: 825.8°C at 760 mmHg
• PKA: 7.38±0.60(Predicted)
• Flash Point: 280°C
• PSA: 200.28000
• Density: 1.68g/cm³
• LogP: -0.35520

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 7-O-ribofuranosyldaunomycinone

There total 7 articles about 7-O-ribofuranosyldaunomycinone 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: 94.0%

7-O-(2,3,5-tri-O-acetyl-D-ribofuranosyl)daunomycinone (105444-01-7) → 7-O-(β-D-ribofuranosyl)daunomycinone (105444-04-0)

Guidance literature:

With sodium hydroxide; In acetone; for 4h;

DOI:10.1016/S0008-6215(00)90210-6

Reference yield:

(+)-Daunomycinone (21794-55-8) → 7-O-(β-D-ribofuranosyl)daunomycinone (105444-04-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / 3A molecular sieves, HgO, HgBr₂ / CH₂Cl₂ / 1 h

2: 94 percent / 0.5 M sodium hydroxide / acetone / 4 h

With sodium hydroxide; 3 A molecular sieve; mercury dibromide; mercury(II) oxide; In dichloromethane; acetone;

DOI:10.1016/S0008-6215(00)90210-6

Reference yield:

2,3,5-tri-O-acetyl-D-ribofuranose (1199614-81-7) → 7-O-(β-D-ribofuranosyl)daunomycinone (105444-04-0)

Guidance literature:

Multi-step reaction with 3 steps

1: bromotrimethylsilane / CH₂Cl₂ / 1.) 10 m, 0 deg C, 2.) 3 h, room temperature

2: 92 percent / 3A molecular sieves, HgO, HgBr₂ / CH₂Cl₂ / 1 h

3: 94 percent / 0.5 M sodium hydroxide / acetone / 4 h

With sodium hydroxide; trimethylsilyl bromide; 3 A molecular sieve; mercury dibromide; mercury(II) oxide; In dichloromethane; acetone;

DOI:10.1016/S0008-6215(00)90210-6

upstream raw materials:

7-O-(5-O-acetyl-β-D-ribofuranosyl)daunomycinone

7-O-(3,5-di-O-acetyl-β-D-ribofuranosyl)daunomycinone

7-O-(2,3,5-tri-O-acetyl-D-ribofuranosyl)daunomycinone

2,3,5-tri-O-acetyl-D-ribofuranosyl bromide

Refernces