6-Deoxydaunomycin

Base Information

• Chemical Name: 6-Deoxydaunomycin
• CAS No.: 71800-91-4
• Molecular Formula: C₂₇H₂₉NO₉
• Molecular Weight: 511.529
• Metabolomics Workbench ID: 114821
• Nikkaji Number: J92.765A
• Mol file: 71800-91-4.mol

Synonyms:11-deoxydaunomycin

Chemical Property of 6-Deoxydaunomycin

Chemical Property:

• Vapor Pressure: 1.01E-23mmHg at 25°C
• Boiling Point: 751.4°C at 760 mmHg
• Flash Point: 408.3°C
• PSA: 165.61000
• Density: 1.49g/cm³
• LogP: 2.02360
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 511.18423150
• Heavy Atom Count: 37
• Complexity: 928

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(CC(O1)OC2CC(CC3=CC4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)(C(=O)C)O)N)O
• Isomeric SMILES: C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=CC4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)(C(=O)C)O)N)O

Technology Process of 6-Deoxydaunomycin

There total 12 articles about 6-Deoxydaunomycin 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: 95.0%

(+)-3'-N-trifluoroacetyl-11-deoxydaunomycin (78098-72-3) → 11-deoxydaunomycin (71800-91-4)

Guidance literature:

With sodium hydroxide; for 0.333333h; Ambient temperature;

DOI:10.1248/cpb.36.3897

Reference yield:

(+/-)-9-<1,1-(ethylenedioxy)ethyl>-cis-6,7,9-trihydroxy-4-methoxy-7,8,9,10-tetrahydronaphthacene-5,12-dione (115043-52-2,115043-53-3) → 11-deoxydaunomycin (71800-91-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 22 percent / TMSOTf, molecular sieves 4 Angstroem / CH₂Cl₂; diethyl ether / 7.5 h

2: 41 percent / aq. 80percent AcOH / 40 h / 45 °C

3: 82 percent / 0.1N NaOH / CH₂Cl₂; methanol / 0.33 h / 0 °C

4: 95 percent / 0.1N NaOH / 0.33 h / Ambient temperature

With sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; acetic acid; In methanol; diethyl ether; dichloromethane;

DOI:10.1248/cpb.36.3897

Reference yield:

2,3,6-trideoxy-1,4-di-O-p-nitrobenzoyl-3-trifluoroacetamido-L-lyxopyranose (52583-22-9) → 11-deoxydaunomycin (71800-91-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 22 percent / TMSOTf, molecular sieves 4 Angstroem / CH₂Cl₂; diethyl ether / 7.5 h

2: 41 percent / aq. 80percent AcOH / 40 h / 45 °C

3: 82 percent / 0.1N NaOH / CH₂Cl₂; methanol / 0.33 h / 0 °C

4: 95 percent / 0.1N NaOH / 0.33 h / Ambient temperature

With sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; acetic acid; In methanol; diethyl ether; dichloromethane;

DOI:10.1248/cpb.36.3897

upstream raw materials:

(+)-3'-N-trifluoroacetyl-11-deoxydaunomycin

2,3,6-trideoxy-1,4-di-O-p-nitrobenzoyl-3-trifluoroacetamido-L-lyxopyranose

1-chloro-2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-L-lyxohexopyranose

(+/-)-9-<1,1-(ethylenedioxy)ethyl>-6,9-dihydroxy-4-methoxy-7,8,9,10-tetrahydronaphthacene-5,12-dione