4'-Epi-daunorubicin

Base Information

• Chemical Name: 4'-Epi-daunorubicin
• CAS No.: 57918-24-8
• Molecular Formula: C27H29 N O10
• Molecular Weight: 527.528
• European Community (EC) Number: 680-677-2
• UNII: ST2WDK731R
• DSSTox Substance ID: DTXSID80206629
• Nikkaji Number: J911.644C
• Wikidata: Q27289384
• ChEMBL ID: CHEMBL3278534
• Mol file: 57918-24-8.mol

Synonyms:4'-Epi-daunorubicin;Epidaunorubicin;57918-24-8;UNII-ST2WDK731R;ST2WDK731R;(7S,9S)-9-acetyl-7-[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;5,12-Naphthacenedione, 8-acetyl-10-((3-amino-2,3,6-trideoxy-beta-L-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, hydrochloride, (8S-cis)-;epi-Daunomycin;Epidauno-rubicin;EPI-DAUNORUBICIN;EPIRUBICIN IMPURITY F;C27H29O10.ClH;CHEMBL3278534;SCHEMBL18537988;DTXSID80206629;LS-93980;W-107590;Q27289384;EPIRUBICIN HYDROCHLORIDE IMPURITY F [EP IMPURITY];EPIRUBICIN HYDROCHLORIDE IMPURITY,EPIDAUNORUBICIN- [USP IMPURITY];(8S,10S)-8-ACETYL-10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-ARABINO-HEXOPYRANOSYL)OXY)-6,8,11-TRIHYDROXY-1-METHOXY-7,8,9,10-TETRAHYDROTETRACENE-5,12-DIONE;5,12-NAPHTHACENEDIONE, 8-ACETYL-10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-ARABINO-HEXOPYRANOSYL)OXY)-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-1-METHOXY-, (8S,10S)-;5,12-Naphthacenedione, 8-acetyl-10-[(3-amino-2,3,6-trideoxy-.alpha.-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8S-cis)-

Chemical Property of 4'-Epi-daunorubicin

Chemical Property:

• Vapor Pressure: 6.13E-25mmHg at 25°C
• Boiling Point: 770°C at 760 mmHg
• Flash Point: 419.5°C
• PSA: 185.84000
• Density: 1.55g/cm³
• LogP: 1.72920
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 527.17914612
• Heavy Atom Count: 38
• Complexity: 960

Purity/Quality:

99% ^*data from raw suppliers

4’-epi-Daunorubicin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(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=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)C)O)N)O

Technology Process of 4'-Epi-daunorubicin

There total 25 articles about 4'-Epi-daunorubicin 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: 98.3%

4'-epi-N-(trifluoroacetyl)daunorubicin (57918-22-6,52471-41-7,64686-33-5) → 4’-epidaunorubicin (57918-24-8)

Guidance literature:

With sodium hydroxide; In water; at 0 - 5 ℃; for 0.833333h;

Reference yield: 90.0%

7-O-<2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-(trifluoroacetamido)-α-L-arabino-hexopyranosyl>daunomycinone (73926-01-9) → 4’-epidaunorubicin (57918-24-8)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 20 ℃; for 1h;

DOI:10.1016/S0008-6215(00)83831-8

Reference yield:

4'-keto-N-trifluoroacetyl-daunorubicin (79441-78-4) → 4’-epidaunorubicin (57918-24-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium triethylborohydride / tetrahydrofuran / 1.67 h / 20 °C

2: sodium hydroxide / water / 0.5 h / 30 °C

With sodium triethylborohydride; sodium hydroxide; In tetrahydrofuran; water;

upstream raw materials:

7-O-<2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-(trifluoroacetamido)-α-L-arabino-hexopyranosyl>daunomycinone

1,5-anhydro-3,4-di-O-benzoyl-2,6-didesoxy-L-arabino-hex-1-enitol

2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-(trifluoroacetamido)-L-arabino-hex-1-enitol

3-amino-1,5-anhydro-2,3,6-tridesoxy-L-arabino-hex-1-enitol

Downstream raw materials:

4'-epi-N-(trifluoroacetyl)daunorubicin

Refernces

• 1、 -. "A epirubicin than star intermediate body surface epidaunorubicin synthetic method (by machine translation)". Paragraph 0098; 0229-0240; 0282-0285. . Retrieved 2019/07/08.
• 2、 -. "Epirubicin hydrochloride intermediate compound IV". Paragraph 0197; 0198; 0199; 0200; 0207; 0208; 0212; 0213. . Retrieved 2017/09/01.