26388-52-3

Basic information

• Product Name: trifluoroacetyldaunomycin
• Synonyms: trifluoroacetyldaunomycin;N-(Trifluoroacetyl)daunorubicin;(8S,10S)-8-Acetyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-Methoxy-10-[[2,3,6-trideoxy-3-[(2,2,2-trifluoroacetyl)aMino]-α-L-lyxo-hexopyranosyl]oxy]-5,12-naphthacenedione
• CAS NO: 26388-52-3
• Molecular Formula: C₂₉H₂₈F₃NO₁₁
• Molecular Weight: 623.5279296
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 26388-52-3.mol
• Article Data: 14

Chemical Properties

• Melting Point: >173°C (dec.)
• Boiling Point: 817°C at 760 mmHg
• Flash Point: 447.9°C
• Appearance: /
• Density: 1.61g/cm³
• Vapor Pressure: 3.15E-28mmHg at 25°C
• Refractive Index: 1.641
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 7.39±0.60(Predicted)
• CAS DataBase Reference: trifluoroacetyldaunomycin(CAS DataBase Reference)
• NIST Chemistry Reference: trifluoroacetyldaunomycin(26388-52-3)
• EPA Substance Registry System: trifluoroacetyldaunomycin(26388-52-3)

Safety Data

• Hazardous Substances Data: 26388-52-3(Hazardous Substances Data)

Usage

Chemical Properties

Red Solid

Uses

Protected Daunorubicin.

InChI:InChI=1/C29H28F3NO11/c1-10-22(35)14(33-27(40)29(30,31)32)7-17(43-10)44-16-9-28(41,11(2)34)8-13-19(16)26(39)21-20(24(13)37)23(36)12-5-4-6-15(42-3)18(12)25(21)38/h4-6,10,14,16-17,22,35,37,39,41H,7-9H2,1-3H3,(H,33,40)/t10-,14-,16-,17-,22+,28-/m0/s1

Upstream product

• 26295-55-6 14-iodo-N-(trifluoroacetyl)daunorubicin 
• 383-63-1 ethyl trifluoroacetate, 
• 23541-50-6 daunomycin hydrochloride 
• 407-25-0 trifluoroacetic anhydride 
• 219921-59-2 3'-N,4'-O-di-trifluoroacetyldaunomycin 
• 20830-81-3 DNR 
• 25561-30-2 N,O-Bis(trimethylsilyl)trifluoroacetamide 

Downstream Products

• 130767-70-3 4'-O-(4-O-Benzoyl-2-bromo-2,6-dideoxy-3-C-methyl-α-D-altropyranosyl)-3'-N-trifluoroacetyldaunomycin 
• 57918-24-8 4’-epidaunorubicin 
• 57852-57-0 idarubicin hydrochloride 
• 68594-06-9 4-demethyl-3'-trifluoroacetamido-daunorubicine 
• 130767-71-4 C₄₃H₄₄F₃NO₁₅ 
• 130767-72-5 Benzoic acid (2R,3R,4S,6R)-6-[(2S,3S,4S,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-4-amino-2-methyl-tetrahydro-pyran-3-yloxy]-4-hydroxy-2,4-dimethyl-tetrahydro-pyran-3-yl ester 
• 83945-38-4 N-[(2S,3R,4R,6R)-6-((1S,3S)-3-Acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-3-hydroxy-2-methyl-tetrahydro-pyran-4-yl]-2,2,2-trifluoro-acetamide 
• 57918-22-6 4'-epi-N-(trifluoroacetyl)daunorubicin 
• 83945-39-5 N-Trifluoracetyldaunorubicin 

Relevant articles and documents

Preparation method for idarubicin hydrochloride

The invention belongs to the field of drug synthesis, and discloses a preparation method for idarubicin hydrochloride. The idarubicin hydrochloride is prepared by adopting a metal nickel catalyst / anorganic phosphine ligand / a silane reducing agent to remove a methoxy group located at a 4-position of an anthracycline compound in one step. According to the invention, the method has the advantages that the steps are short and the synthesis costs are reduced, can reduce generation of an impurity A and an impurity B, and improves the quality of the final product idarubicin hydrochloride.

Epirubicin hydrochloride intermediate compound IV

The invention provides a novel intermediate and a new route for synthesizing epirubicin hydrochloride by using the intermediate. The route is simple, cheap and efficient, and meanwhile, the problems that the intermediate generated by an existing epirubicin hydrochloride synthesis route is instable in water and easy to decompose and the whole route is low in yield are solved. In order to better achieve energy conservation and emission reduction, a cheap and available reagent is utilized by the route; and meanwhile, removable selective protection means are adopted, so that the generated impurities are few, the purity is high and the yield is high.

METHOD OF PRODUCING 4-DEMETHOXYDAUNORUBICIN

The present invention relates to a method for the synthesis of 4-demethoxydaunorubicin (idarubicin) having the chemical structure of formula (I), which involves the demethylation of 3′-Prot-daunorubicin in the presence of a soft Lewis acid. The method of the present invention does not comprise cleavage of the glycosidic linkage at carbon C7, thus resulting in a faster synthesis cycle and an improved yield of the final product.