57918-24-8

Basic information

• Product Name: (1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranoside
• Synonyms: 4’-epi-Daunorubicin;Epirubicin EP Impurity F;5,12-Naphthacenedione, 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-, (8S,10S)-
• CAS NO: 57918-24-8
• Molecular Formula: C₂₇H₂₉NO₁₀
• Molecular Weight: 527.5199
• Mol File: 57918-24-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 770°C at 760 mmHg
• Flash Point: 419.5°C
• Density: 1.55g/cm³
• Vapor Pressure: 6.13E-25mmHg at 25°C
• Refractive Index: 1.691
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• Stability: Light Sensitive
• CAS DataBase Reference: (1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranoside(57918-24-8)
• EPA Substance Registry System: (1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranoside(57918-24-8)

Safety Data

• Hazardous Substances Data: 57918-24-8(Hazardous Substances Data)

Upstream product

• 57918-22-6 4'-epi-N-(trifluoroacetyl)daunorubicin 
• 59492-30-7 methyl (5S)-2,3,6-trideoxy-α-L-glycero-hexopyranosid-4-ulose 
• 56354-07-5 Methyl 2,3,6-trideoxy-3-trifluoroacetamido-α-L-threo-hexopyranoside-4-ulose 
• 55102-46-0 methyl 2,3,6-trideoxy-α-L-glycero-hex-2-enopyranosid-4-ulose 
• 79441-78-4 4'-keto-N-trifluoroacetyl-daunorubicin 
• 26388-52-3 3'-N-trifluoroacetyldaunorubicin 
• 23541-50-6 daunomycin hydrochloride 
• 14218-08-7 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl bromide 
• 73864-38-7 2,3,6-tridesoxy-3-(trifluoroacetamido)-L-arabino-hex-1-enitol 
• 73864-37-6 3-amino-1,5-anhydro-2,3,6-tridesoxy-L-arabino-hex-1-enitol 
• 73891-04-0 2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-(trifluoroacetamido)-L-arabino-hex-1-enitol 
• 34820-21-8 1,5-anhydro-3,4-di-O-benzoyl-2,6-didesoxy-L-arabino-hex-1-enitol 
• 73926-01-9 7-O-<2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-(trifluoroacetamido)-α-L-arabino-hexopyranosyl>daunomycinone 

Downstream Products

• 57918-22-6 4'-epi-N-(trifluoroacetyl)daunorubicin 

Relevant articles and documents

A epirubicin erythromycin intermediate compound

The invention belongs to the field of organic chemistry, and in particular discloses a key intermediate epirubicin of erythromycin, its synthetic method and preparing the use of erythromycin in the epirubicin. The one preferred embodiment of this invention to (2 R, 6 S) - 6 - methoxy - 2 - methyl - 6 H - pyran - 3 - ons starting material, through reducing the double bond, halogenated, ammoniation, chiral separation, through the trifluoroacetyl group for protecting amino group, chloro can be obtained after the intermediate VI, with intermediate VI [...] by sodium borohydride reduction, de-trifluoroacetic acyl shall epirubicin than star intermediate body surface daunomycin. The full synthetic route has the short steps, mild reaction conditions, high yield, after treatment is convenient and the like, has good industrial prospects.

Epirubicin hydrochloride than star-intermediate compound (by machine translation)

The present invention provides novel intermediates and utilizing the intermediate synthesis than the star of epirubicin hydrochloride new routes. The route is simple, low-cost, high-efficiency, at the same time avoiding the existing epirubicin hydrochloride than star-synthetic route to produce the intermediate with water not stable, easily decomposed, the overall line rate is on the low side, in order to better energy-saving and emission reduction, the routes using low cost and easily obtained reagent; at the same time adopts the removable selective protection means, produce little impurity, high purity, high yield. (by machine translation)

EPIMERIZATION OF 4'-C BOND AND MODIFICATION OF 14-CH3-(CO)-FRAGMENT IN ANTHRACYCLIN ANTIBIOTICS

A method of synthesizing Rl, R2-substituted-4' (ax. or eq.)-OH anthracyclines and their corresponding salts of Formula (1) from daunorubicin or N-Trifluoroacetyl-4- Rl - derivatives of daunorubicin, wherein Rl is defined as H, OH, and 4'-HO is defined as ax[ial]. The method includes producing N-Trifluoroacetyl daunorubicin and treating the N- Trifluoroacetyldaunorubicin or N-Trifluoroacetyl-4-R1 -derivatives of daunorubicin, wherein R1 is defined as H, OH, with dimethylsulfoxide activated by different acylating agents. The attained intermediate product is then treated with a strong base (ex. tertiary amines) resulting in the 4 -keto-N-Trifluoroacetyl-4-R1 daunorubicin wherein Ri is defined as H, OH, OMe. The 4-keto-N-Trifluoroacetyl-4-R1 -daunorubicin is reacted with a reducing agent, a derivative of a borohydride of an alkaline metal MHBL3 ,to produce N- Trifluoroacetyl-4'-epi-4-R1 -daunorubicin. The N-Trifluoroacetyl-4'-epi-4-R1 -daunorubicin undergoes hydrolysis in a basic solution to produce a derivate of an anthoacyclin which is halogenized [by complex halogenidesjto form a 14-Hal-derivative. This result is then hydrolyzed by well-known methods in the presence of a formate of an alkaline metal to form the desired final compound.