56390-08-0

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

Downstream Products

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

Relevant academic research and scientific papers

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.

Process for the preparation of 4'-epidaunorubicin, 3',4'-diepidaunorubicin, their doxorubicin analogs, and intermediates used in said process

Disclosed is a process for preparing the known antitumor glycosides: 4'-epidaunorubicin, 3',4'-diepidaunorubicin, and their doxorubicin analogs by oxidizing the C-4' hydroxyl group of N-protected daunorubicin to form certain novel intermediates having a 4'-keto configuration, followed by reduction of the keto group with NaBH4 and mild alkaline hydrolysis to remove the N-protecting acyl groups.

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.

HEMISYNTHESE DE NOUVEAUX GLICOSIDES ANALOGUES DE LA DAUNORUBICINE

Seven daunorubicin analogs containing α-L-, α-D-, and β-D-glicosidic linkages, in which the natural occuring sugar (L-daunosamine) was replaced by diastereomeric 3-amino-2,3,6-trideoxyhexoses (3-epi-L-daunosamine, D-acosamine, D-daunosamine, D-ristosamine, and 3-epi-D-daunosamine), were prepared.In all cases, glycosidation with daunomycinone was performed in the presence of p-toluenesulfonic acid starting from 1-O-acetyl-2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoro-acetamidohexopyranoses (prepared from the corresponding methyl 3-amino-2,3,6-trideoxyhexopyranosides) or from 1,5-anhydro-2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamidohex-1-enitols (prepared from glycosals or pseudoglycals, the 3-amino group being introduced by substitution with sodium azide and subsequent reduction).Glycosidation was followed by removal of the protecting groups.