56390-08-0

Basic information

• Product Name: (8S-cis)-8-acetyl-10-[(3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxynaphthacene-5,12-dione hydrochloride
• Synonyms: (8S-cis)-8-acetyl-10-[(3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxynaphthacene-5,12-dione hydrochloride;4'-Epi-daunomycin hydrochloride;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-, hydrochloride, (8S-cis)-;Nsc249333;Replaced cas registry number(S): 62414-04-4;4'-epi-Daunorubicin Hydrochloride;(8S,10S)-8-Acetyl-10-[(3-aMino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-Methoxy-5,12-naphthacenedione Hydrochloride;(8S-cis)-4'-Epidaunorubicin Hydrochloride
• CAS NO: 56390-08-0
• Molecular Formula: C₂₇H₃₀NO₁₀*Cl
• Molecular Weight: 563.984
• EINECS: 260-144-7
• Product Categories: Carbohydrates & Derivatives;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 56390-08-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 770 °C at 760 mmHg
• Flash Point: 419.5 °C
• Appearance: /
• Vapor Pressure: 6.99E-26mmHg at 25°C
• CAS DataBase Reference: (8S-cis)-8-acetyl-10-[(3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxynaphthacene-5,12-dione hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (8S-cis)-8-acetyl-10-[(3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxynaphthacene-5,12-dione hydrochloride(56390-08-0)
• EPA Substance Registry System: (8S-cis)-8-acetyl-10-[(3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxynaphthacene-5,12-dione hydrochloride(56390-08-0)

Safety Data

• Hazardous Substances Data: 56390-08-0(Hazardous Substances Data)

Usage

Uses

Daunorubicin (D194500) impurity. Daunomycin analog antitumor.

InChI:InChI=1/C27H29NO10.ClH/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33;/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3;1H/t10-,14-,16-,17-,22-,27-;/m0./s1

Upstream product

• 21794-55-8 (+)-Daunomycinone 
• 108-24-7 acetic anhydride 
• 76753-25-8 2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-D-lyxo-hexopyranose 
• 6605-27-2 methyl-3-acetamido-2,3,6-tridesoxy-α-D-lyxo-hexopyranoside 
• 76793-38-9 methyl-3-amino-2,3,6-tridesoxy-α-D-lyxo-hexopyranoside 
• 76793-39-0 methyl-2,3,6-tridesoxy-3-trifluoroacetamido-α-D-lyxo-hexopyranoside 
• 76753-28-1 methyl-2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-α-D-lyxo-hexopyranoside 
• 62445-20-9 7-O-<2,3,6-tridesoxy-4'-O-p-nitrobenzoyl-3-(trifluoroacetamido)-α-L-ribo-hexopyranosyl>daunomycinone 
• 34820-21-8 1,5-anhydro-3,4-di-O-benzoyl-2,6-didesoxy-L-arabino-hex-1-enitol 
• 73891-07-3 2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-(trifluoroacetamido)-L-ribo-hex-1-enitol 
• 73864-37-6 3-amino-1,5-anhydro-2,3,6-tridesoxy-L-ribo-hex-1-enitol 
• 73891-06-2 2,3,6-tridesoxy-3-(trifluoroacetamido)-L-ribo-hex-1-enitol 
• 14218-08-7 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl bromide 
• 57918-22-6 4'-epi-N-(trifluoroacetyl)daunorubicin 

Downstream Products

• 99530-17-3 C₂₇H₂₈BrNO₁₀*ClH 
• 99570-29-3 C₂₇H₂₈BrNO₁₀ 

Relevant articles and documents

SYNTHESIS OF EPIRUBICIN FROM 13-DIHYDRODAUNORUBICINE

A method of preparing an anthracyclin such as epirubicin from a starting material comprising 13-dihydrodaunorubicine (13-daunorubicinol). The method comprises producing N-Trifluoroacetyl-13-daunorubicinol from 13-daunorubicinol by acylation. The N-Trifluoroacetyl-13-daunorubicinol is reacted with an aprotic solvent and an acylating agent to produce an intermediate sulfoxy salt which is treated with a strong base to produce 4′-keto-N-Trifluoroacetyldaunorubicin. The 4′-keto-N-Trifluoroacetyldaunorubicin is reacted with a reducing agent, such as borohydride of an alkaline metal, to produce N-Trifluoroacetyl-4′-epi-daunorubicin. The N-Trifluoroacetyl-4′-epi-daunorubicin is hydrolyzed in a basic solution to produce an intermediate compound. The intermediate compound is reacted with a halogenizing agent to produce a 14-Hal-derivative. The 14-Hal derivative is hydrolized in the presence of a formate of an alkaline metal to produce the desired final compound.

SUBSTITUTIONS D'ESTERS ALLYLIQUES: PREPARATION DE GLYCALS AMINES EN C-3 ET ETUDE DE LEUR GLYCOSIDATION ACIDO-CATALYSEE. APPLICATION A L'HEMISYNTHESE DE GLYCOSIDES DU GROUPE DES ANTHRACYCLINES

3-Amino-1,5-anhydro-2,3,6-trideoxy-L-arabino- and -L-ribo-hex-1-enitol were prepared by substitution of the allylic ester function of 1,5-anhydro-3,4-di-O-benzoyl-2,6-dideoxy-L-arabino-hex-1-enitol with sodium azide, followed by reduction with lithium aluminium hydride.Glycosidation was performed with various alcohols, in particular daunomycinone.In the latter case, the partial synthesis of 4'-epi- and 3',4'-epi-daunorubicines was accomplished in three major steps.