64686-33-5

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 2,3,6-trideoxy-3-[(trifluoroacetyl)amino]-alpha-L-lyxo-hexopyranoside
• Synonyms: 5,12-naphthacenedione, 8-acetyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-10-[[2,3,6-trideoxy-3-[(2,2,2-trifluoroacetyl)amino]-alpha-L-lyxo-hexopyranosyl]oxy]-, (8S,10S)-
• CAS NO: 64686-33-5
• Molecular Formula: C₂₉H₂₈F₃NO₁₁
• Molecular Weight: 623.5279
• Mol File: 64686-33-5.mol

Chemical Properties

• Boiling Point: 817°C at 760 mmHg
• Flash Point: 447.9°C
• Density: 1.61g/cm³
• Vapor Pressure: 3.15E-28mmHg at 25°C
• Refractive Index: 1.641
• 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 2,3,6-trideoxy-3-[(trifluoroacetyl)amino]-alpha-L-lyxo-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 2,3,6-trideoxy-3-[(trifluoroacetyl)amino]-alpha-L-lyxo-hexopyranoside(64686-33-5)
• 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 2,3,6-trideoxy-3-[(trifluoroacetyl)amino]-alpha-L-lyxo-hexopyranoside(64686-33-5)

Safety Data

• Hazardous Substances Data: 64686-33-5(Hazardous Substances Data)

Upstream product

• 26295-55-6 14-iodo-N-(trifluoroacetyl)daunorubicin 
• 23541-50-6 daunomycin hydrochloride 
• 407-25-0 trifluoroacetic anhydride 
• 20830-81-3 DNR 
• 25561-30-2 N,O-Bis(trimethylsilyl)trifluoroacetamide 
• 79441-78-4 4'-keto-N-trifluoroacetyl-daunorubicin 
• 26388-52-3 3'-N-trifluoroacetyldaunorubicin 
• 79516-72-6 N-[(2S,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)-2-methyl-3-oxo-tetrahydro-pyran-4-yl]-2,2,2-trifluoro-acetamide 
• 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 
• 57918-24-8 4’-epidaunorubicin 
• 383-63-1 ethyl trifluoroacetate, 

Downstream Products

• 83945-39-5 N-Trifluoracetyldaunorubicin 
• 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 
• 57918-24-8 4’-epidaunorubicin 
• 68594-06-9 4-demethyl-3'-trifluoroacetamido-daunorubicine 

Relevant articles and documents

Synthesis of 4'-epi-iodo-4'-deoxy-daunorubicin, a potential cancer radiotherapeutic agent

We have prepared 4'-epi-iodo-4'-deoxy-daunorubicin (IDDNR)(1), a doxorubicin analog, via a 5-step synthesis involving a protected daunorubicin triflate derivative (4). This triflate derivative will allow the facile and regiospecific nucleophilic preparation of I-125 or Br-80m labelled analogs of IDDNR. Auger electronemitting I-125- or Br-80m-labelled analogs of IDDNR may have potential as cancer radiotherapeutic agents.

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.

A epirubicin than star intermediate body surface epidaunorubicin synthetic method (by machine translation)

The invention belongs to the field of organic synthesis, in particular discloses a epirubicin than star intermediate body surface epidaunorubicin synthetic method. The invention relates 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, to remove trifluoroacetic acyl shall epirubicin than star intermediate body surface daunomycin. The invention fully synthetic route has the short steps, mild reaction conditions, high yield, after treatment is convenient and the like, has good industrial prospects. (by machine translation)

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 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)

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.

A kind of N - trifluoro acetyl epirubicin seleno derivatives of erythromycin, preparation method and application thereof

The invention discloses a seleno derivative of N-trifluoroacetyl epidaunorubicin, and adopts the structure of a general formula I (shown in the Specification). According to the invention, through the reaction of epidaunorubicin and trifluoroacetyl, an N-trifluoroacetyl epidaunorubicin is generated for reacting with a corresponding substituted seleno acetic acid so as to generate the N-trifluoroacetyl epidaunorubicin seleno derivative, wherein a substituent group being a seleno compound, is introduced through N-trifluoroacetyl epidaunorubicin 4' isotope for synthetizing the N- trifluoroacetyl epidaunorubicin seleno derivative in the hope of screening out anti-cancer drugs good in antitumor activity. The synthesis method provided by the invention is simple and scientific, and facilitates industrial production; the N-trifluoroacetyl epidaunorubicin seleno derivative can be used for the treatment of malignant tumors in the field of medicine.

A hydrochloric acid the table is supple than star process for the preparation of intermediates

The invention relates to a preparation method for an intermediate 4'-epidaunorubicin hydrochloride of epirubicin hydrochloride. The preparation method comprises the steps of trifluoroacetyl protection, oxidation, reduction, hydrolyzation, etc. The method effectively inhibit generation of (methylthio)methyl ether, increases selectivity for sodium borohydride during the reduction process and is mild in reaction conditions. The total yield of the reaction is over 40% (based on epidaunorubicin hydrochloride) and the purity reaches 99.5%.

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.

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.