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Daunorubicin hydrochloride
Cas No: 23541-50-6
USD $ 2.0-2.0 / Gram 1 Gram 1 Metric Ton/Week GIHI CHEMICALS CO.,LIMITED Contact Supplier
Daunorubicin Hydrochloride 23541-50-6
Cas No: 23541-50-6
No Data 100 Gram 1 Kilogram/Week JINING XINHE CHEMICAL CO., LTD Contact Supplier
Daunorubicin hydrochloride Manufacturer/High quality/Best price/In stock
Cas No: 23541-50-6
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
Daunorubicin hydrochloride
Cas No: 23541-50-6
USD $ 0.9-1.0 / Kilogram 1 Kilogram 1000 Kilogram/Month LIDE PHARMACEUTICALS LIMITED Contact Supplier
Daunorubicin hydrochloride injection 20mg/4ml;50mg/10ml
Cas No: 23541-50-6
No Data 1 Gram 1000 Metric Ton/Month Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd Contact Supplier
Daunorubicin hydrochloride CAS NO.23541-50-6
Cas No: 23541-50-6
USD $ 1.0-3.0 / Metric Ton 1 Metric Ton 10 Metric Ton/Day Hebei yanxi chemical co.,LTD. Contact Supplier
Daunorubicin hydrochloride CAS 23541-50-6
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USD $ 10.0-10.0 / Kilogram 10 Kilogram 300 Metric Ton/Year Wuhan Fortuna Chemical Co.,Ltd Contact Supplier
Daunorubicin hydrochloride
Cas No: 23541-50-6
No Data No Data No Data Chemwill Asia Co., Ltd. Contact Supplier
High Quality 99% Daunorubicin hydrochloride 23541-50-6 GMP manufacturer
Cas No: 23541-50-6
USD $ 0.1-0.1 / Gram 1 Gram 100 Metric Ton/Year Xi'an Xszo Chem Co., Ltd. Contact Supplier
Factory Supply Daunorubicin Hydrochloride
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23541-50-6 Usage

Reactivity Profile

Daunorubicin hydrochloride may emit toxic oxides of nitrogen when heated.

Manufacturing Process

A 170 liter fermentation vessel is charged with:Corn steep2.400 kgSucrose3.600 kgCalcium carbonate0.900 kgAmmonium sulphate 0.240 kgWaterto 100 litersThis culture medium has a pH of 6.15. It is sterilised by passage of steam at 122°C for 40 minutes. After cooling, the volume of the broth is 120 liters and the pH is 7.20. The medium is then seeded with 200 cc of a culture of the strain Streptomyces 31723. The culture is carried out for 27 hours at 26°- 27°C with agitation and aeration with sterile air. It is then suitable for seeding the production culture. The production culture is carried out in an 800 liter formentation vessel charged with the following:Soya flour 20 kgDistillers' solubles 2.500 kgSoya oil 2.500 litersSoya oil 2.500 litersSodium chloride 5 kgWater to 465 litersStarch 10 kgThe pH of the medium thus obtained is adjusted to 7.20 with concentrated sodium hydroxide solution (400 cc). The medium is then sterilised by the passage of steam at 122°C for 40 minutes. After cooling, the volume of the broth is 500 liters and the pH is 6.75. It is then seeded with 50 liters of the culture from the 170 liter fermentation vessel. Culture is carried out at 28°C for 67 hours with agitation and aeration with sterile air. The pH of the medium is then 7.40 and the volume of the fermentation culture is 520 liters. The quantitiy of antibiotic present in the medium is 29 μ/cc.The above fermentation culture (520 liters; activity 29 μ/cc) is placed in a vessel equipped with an agitator and the pH is adjusted to 1.8 with a concentrated solution of oxalic acid. Agitation is carried out for one hour and a filtration adjuvant (20 kg) then added. The mixture is filtered on a filter-press and the filter-cake washed with water (100 liters) acidified to pH 2 with oxalic acid. The filtrate (612 liters) is treated with concentrated sodium hydroxide solution until the pH is 4.5. The filtrate is then passed through a column containing Amberlite IRC 50 in hydrogen form (20 liters; diameter of column 15.2 cm, height of column 200 cm, height of resin at rest in column 110 cm). The filtrate passes through the bed of Amberlite from base to top at a rate of 40 liters/hour. The column is then washed with water (100 liters) at a rate of 50 liters/hour circulating from base to top and then with methanol (containing 10% water; 75 liters) circulating from top to base at a rate of 50 liters/hour. The washings are discarded and the column is then eluted with a solution having the following composition (per liter):The eluate (100 liters), which contains the major part of the antibiotic, is concentrated under reduced pressure at 35°C to 10 liters. The concentrate is extracted at pH 7.5 with chloroform (2 times 5 liters). The chloroformic extract is adjusted to pH 4 with a solution of acetic acid in chloroform (10:100 by volume) and then concentrated at 30°C under reduced pressure to 100 cc. The antibiotic is precipitated by the addition of hexane (1 liter), separated, washed and dried to give an amorphous red powder (9 g) of activity 1,400 μ/mg.The crude antibiotic (17.1 g) obtained as above described (activity 1530 μ/mg) is dissolved with stirring in a mixture of methylene chloride (1.5 liters), carbon tetrachloride (0.3 liters) and water (1.8 liters). The pH is then adjusted9865 RP (500 mg), obtained as above described, is dissolved in normal sulphuric acid (100 cc) and the solution obtained is heated for 20 minutes on a water-bath. After cooling and extracting with ethyl acetate (3 times 200 cc), the organic extract is dried over anhydrous sodium sulphate, filtered and concentrated to a small volume, giving, after filtering, washing and drying, crystals (218.5 mg). These crystals (150 mg) are dissolved in chloroform (3 cc) and benzene (1.5 cc) and the solution obtained is chromatographed on 20 sheets of Arches No. 310 paper impregnated with a solution of acetone containing 20% formamide, and developed for 90 minutes by means of a 2:1 mixture of chloroform and benzene saturatd with formamide. The principal zone of Rf = 0.86 is cut out of each of the 20 sheets and the 20 zones thus cut out are comminuted in a mixer in the presence of methanol. The mixture obtained is filtered, concentrated, and water (10 volumes) added. The precipitate obtained is filtered off, washed and dried under reduced pressure to give crystals (120 mg). These crystals (170 mg) are dissolved in dioxan containing 20% water (15 cc) and water acidified to pH 4 with 0.1 N hydrochloric acid is added dropwise. The crystals formed are filtered off, washed and dried, thus giving the aglycone of 9865 RP (130 mg) in the form of orange-red needles, having a first melting point at 160°C and a second at 225°C-230°C.Daudorubicin can be prepared by gene ingineering methods also. to 3 by the addition of normal hydrochloric acid (8 cc). After decanting, the aqueous phase is treated with methylene chloride (7 liters) and 0.1 N sodium hydroxide solution (200 cc) to give a pH of 7.5. After decanting, the aqueous phase is again extracted at pH 7.5 with methylene chloride (3.5 liters). The methylene chloride extracts are combined and concentrated to 100 cc. After the addition of hexane (1 liter) to the concentrate, a product precipitates which is filtered off, washed and dried at 30°C under reduced pressure to give the antibiotic 9865 RP (9.15 g) in the form of an amorphous orange-red powder of activity 2180 μ/mg.

Uses

Antineoplastic;DNA intercaling

Pharmacokinetics

Like Doxil (the liposomal formulation of doxorubicin), DaunoXome is indicated for use in AIDS-related Kaposi's sarcoma and is administered IV at a dose of 40 mg/m2 every 2 weeks. The pharmacokinetic profiles of Doxil and DaunoXome are similar.

Therapeutic Function

Antineoplastic

Brand name

Cerubidine (Bedford); Cerubidine (Sanofi Aventis); Cerubidine (Wyeth).

General Description

Orange-red powder. Thin red needles decomposing at 188-190°C. An anti-cancer drug.

Biological Activity

Anticancer agent that is clinically used to treat nonlymphocytic leukaemia. Inhibits RNA and DNA synthesis and causes DNA fragmentation in vivo .

Chemical Properties

Dark Red Crystals

Uses

A DNA intercalator which may suppress acute leukemia proliferation

General Description

Daunorubicin is available in 20- and 100-mg vials for reconstitution.The agent is given intravenously for the treatmentof acute nonlymphocytic and lymphocytic leukemia. Otherunlabeled uses include CML and Kaposi sarcoma. In general,its use is more limited than that of doxorubicin.Daunorubicin lacks the hydroxyl groups found at C-14 ofdoxorubicin. This leads to an increase in the amount of thealcohol metabolite daunorubicinol (active) arising as a resultof reduction of the side chain ketone. This, however, doesnot appear to lead to a significant increase in the occurrenceof cardiotoxicity compared with doxorubicin. The mechanismsof resistance and toxicities of daunorubicin are similarto that of doxorubicin; the major difference betweenthe two agents being the spectrum of cancers that they areused treat.A liposomal form of daunorubicin is also availableknown as DaunoXome. The drug offers the same advantagesas those seen for the liposomal form of doxorubicin.

Originator

Cerubidine,Rhone-Poulenc Rorer,France

Clinical Use

Daunorubicin is administered IV at a dose of 45 mg/m2 for the treatment of lymphocytic and nonlymphocytic leukemia.

Uses

anti-neoplastic LD50 in mice 26 mg/kg

Metabolism

The 18.5-hour terminal half-life of daunorubicin is approximately half that of doxorubicin, and the terminal half-life of the active daunorubicinol metabolite is 26.7 hours. Excretion is approximately 40% biliary and 25% urinary.

Air & Water Reactions

Water soluble.

Uses

Anthracycline antibiotic related to the rhodomycins. Antineoplastic
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-;/m1./s1

23541-50-6 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (D4532)  Daunorubicin Hydrochloride  >98.0%(HPLC)(N) 23541-50-6 20mg 990.00CNY Detail
TCI America (D4532)  Daunorubicin Hydrochloride  >98.0%(HPLC)(N) 23541-50-6 100mg 2,990.00CNY Detail
USP (1164700)  Daunorubicinhydrochloride  United States Pharmacopeia (USP) Reference Standard 23541-50-6 1164700-200MG 14,262.30CNY Detail

23541-50-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Daunorubicin hydrochloride(BICINS)

1.2 Other means of identification

Product number -
Other names DAUNOBLASTINE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:23541-50-6 SDS

23541-50-6Synthetic route

Benzoic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride
36508-71-1

Benzoic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride

A

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

B

benzoic acid hydrazide
613-94-5

benzoic acid hydrazide

Conditions
ConditionsYield
With water at 37℃; Rate constant; also half-conversion period, pH 5.58, 0.01 M phosphate buffer;
Nicotinic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride
110925-43-4

Nicotinic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride

A

Nicotinic acid hydrazide
553-53-7

Nicotinic acid hydrazide

B

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

Conditions
ConditionsYield
With water at 37℃; Rate constant; also half-conversion period, pH 5.58, pH 6.80, pH 7.35, 0.01 M phosphate buffer;
Isonicotinic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride
110925-39-8

Isonicotinic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride

A

isoniazid
54-85-3

isoniazid

B

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

Conditions
ConditionsYield
With water at 37℃; Rate constant; also half-conversion period, pH 5.58, pH 6.80, pH 7.35, 0.01 M phosphate buffer;
4-Amino-benzoic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride
110925-32-1

4-Amino-benzoic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride

A

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

B

4-aminobenzohydrazide
5351-17-7

4-aminobenzohydrazide

Conditions
ConditionsYield
With water at 37℃; Rate constant; also half-conversion period, pH 5.58, 0.01 M phosphate buffer;
4-Hydroxy-benzoic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride
66996-57-4

4-Hydroxy-benzoic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride

A

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

B

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

Conditions
ConditionsYield
With water at 37℃; Rate constant; also half-conversion period, pH 5.58, 0.01 M phosphate buffer;
3-[1-[(2S,4S)-4-((2R,4S,5S,6S)-4-Amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene-hydrazinocarbonyl]-benzoic acid ethyl ester; hydrochloride
110925-36-5

3-[1-[(2S,4S)-4-((2R,4S,5S,6S)-4-Amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene-hydrazinocarbonyl]-benzoic acid ethyl ester; hydrochloride

A

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

B

ethyl m-hydrazinecarbonyl benzoate
110925-44-5

ethyl m-hydrazinecarbonyl benzoate

Conditions
ConditionsYield
With water at 37℃; Rate constant; also half-conversion period, pH 5.58, 0.01 M phosphate buffer;
4-[1-[(2S,4S)-4-((2R,4S,5S,6S)-4-Amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene-hydrazinocarbonyl]-benzoic acid ethyl ester; hydrochloride
110925-37-6

4-[1-[(2S,4S)-4-((2R,4S,5S,6S)-4-Amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene-hydrazinocarbonyl]-benzoic acid ethyl ester; hydrochloride

A

4-hydrazinocarbonyl-benzoic acid ethyl ester
19827-16-8

4-hydrazinocarbonyl-benzoic acid ethyl ester

B

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

Conditions
ConditionsYield
With water at 37℃; Rate constant; also half-conversion period, pH 5.58, 0.01 M phosphate buffer;
daunoform
193743-47-4

daunoform

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

Conditions
ConditionsYield
Stage #1: daunoform In dimethylsulfoxide-d6; water-d2 for 24h;
Stage #2: With hydrogenchloride In dimethylsulfoxide-d6; water-d2
daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

3'-N,4'-O-di-trifluoroacetyldaunomycin
219921-59-2

3'-N,4'-O-di-trifluoroacetyldaunomycin

Conditions
ConditionsYield
In dichloromethane at -2 - 2℃; for 1h; Inert atmosphere;100%
In dichloromethane at -2 - 2℃; for 1h; Inert atmosphere;100%
In dichloromethane at 0℃; for 1.5h;
Pyr-His-Trp-Tyr-D-Lys(NH2-O-CH2-CO-Gly-Phe-Leu-Gly)Trp-Tyr-Pro-Gly-NH2

Pyr-His-Trp-Tyr-D-Lys(NH2-O-CH2-CO-Gly-Phe-Leu-Gly)Trp-Tyr-Pro-Gly-NH2

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

[D-Lys6(Dau=Aoa-GFLG)]GnRH-II

[D-Lys6(Dau=Aoa-GFLG)]GnRH-II

Conditions
ConditionsYield
In aq. acetate buffer at 20℃; for 24h; pH=5.2;100%
Pyr-His-Trp-Tyr-D-Lys(NH2-O-CH2-CO-)Leu-Arg-Pro-Gly-NH2

Pyr-His-Trp-Tyr-D-Lys(NH2-O-CH2-CO-)Leu-Arg-Pro-Gly-NH2

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

[D-Lys6(Dau=Aoa)]GnRH-I

[D-Lys6(Dau=Aoa)]GnRH-I

Conditions
ConditionsYield
In aq. acetate buffer at 20℃; for 24h; pH=5.2;100%
Pyr-His-Trp-Tyr-D-Lys(NH2-O-CH2-CO-Gly-Phe-Leu-Gly)Leu-Arg-Pro-Gly-NH2

Pyr-His-Trp-Tyr-D-Lys(NH2-O-CH2-CO-Gly-Phe-Leu-Gly)Leu-Arg-Pro-Gly-NH2

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

[D-Lys6(Dau=Aoa-GFLG)]GnRH-I

[D-Lys6(Dau=Aoa-GFLG)]GnRH-I

Conditions
ConditionsYield
In aq. acetate buffer at 20℃; for 24h; pH=5.2;100%
Pyr-His-Trp-Tyr-D-Lys(NH2-O-CH2-CO-)Trp-Tyr-Pro-Gly-NH2

Pyr-His-Trp-Tyr-D-Lys(NH2-O-CH2-CO-)Trp-Tyr-Pro-Gly-NH2

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

[D-Lys6(Dau=Aoa)]GnRH-II

[D-Lys6(Dau=Aoa)]GnRH-II

Conditions
ConditionsYield
In aq. acetate buffer at 20℃; for 24h; pH=5.2;100%
daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

3'-N-trifluoroacetyldaunorubicin
26388-52-3

3'-N-trifluoroacetyldaunorubicin

Conditions
ConditionsYield
With pyridine In diethyl ether at -20℃; for 0.166667h;99%
With pyridine at -20℃; for 0.5h;95%
With pyridine at -20℃;95%
daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

(+)-Daunomycinone
21794-55-8

(+)-Daunomycinone

Conditions
ConditionsYield
With hydrogenchloride at 90 - 95℃; for 3.5h;98%
With hydrogenchloride at 90℃; for 1h; Hydrolysis;93%
With hydrogenchloride at 90℃; for 1h;92%
daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

Aloc-D-Ala-Phe-Lys(Aloc)-p-aminobenzyl oxycarbonyl p-nitrophenyl carbonate
253863-34-2

Aloc-D-Ala-Phe-Lys(Aloc)-p-aminobenzyl oxycarbonyl p-nitrophenyl carbonate

C61H70N6O19
253863-28-4

C61H70N6O19

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; triethylamine for 16h; Substitution;97%
daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

N-2-biphenyl-2'-carboxylic acid O-(methyl 2,3,4-tri-O-acetyl β-D-glucuronyl) carbamate
320401-53-4

N-2-biphenyl-2'-carboxylic acid O-(methyl 2,3,4-tri-O-acetyl β-D-glucuronyl) carbamate

A

6(5H)-phenanthridinone
1015-89-0

6(5H)-phenanthridinone

B

3,4,5-triacetoxy-6-[6-(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-ylcarbamoyloxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

3,4,5-triacetoxy-6-[6-(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-ylcarbamoyloxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethaneA n/a
B 95%
daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

C30H30F3NO10

C30H30F3NO10

Conditions
ConditionsYield
With pyridine at -20℃; for 0.25h;95%
ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

3'-N-trifluoroacetyldaunorubicin
26388-52-3

3'-N-trifluoroacetyldaunorubicin

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 4h;95%
daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

(E)-4-pentachlorophenyl 5,6-bis<4-(tert-butyldimethylsiloxy)phenyl>-5-octenoate
120743-59-1

(E)-4-pentachlorophenyl 5,6-bis<4-(tert-butyldimethylsiloxy)phenyl>-5-octenoate

(E)-5,6-Bis-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-oct-5-enoic acid [(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)-3-hydroxy-2-methyl-tetrahydro-pyran-4-yl]-amide
120743-62-6

(E)-5,6-Bis-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-oct-5-enoic acid [(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)-3-hydroxy-2-methyl-tetrahydro-pyran-4-yl]-amide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 17h; Ambient temperature;94%
acetic anhydride
108-24-7

acetic anhydride

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

Pentaacetyl-daunomycin
32469-19-5

Pentaacetyl-daunomycin

Conditions
ConditionsYield
With pyridine; dmap for 120h;92%
daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

(S)-2-[4-(4-Nitro-phenoxycarbonyloxymethyl)-phenoxycarbonylamino]-pentanedioic acid diallyl ester
180839-21-8

(S)-2-[4-(4-Nitro-phenoxycarbonyloxymethyl)-phenoxycarbonylamino]-pentanedioic acid diallyl ester

N-<4-(dipropen-2-yl-L-glutamylcarbonyloxy)benzyloxycarbonyl>daunorubicin

N-<4-(dipropen-2-yl-L-glutamylcarbonyloxy)benzyloxycarbonyl>daunorubicin

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide for 3.5h; Ambient temperature;92%
3-(2'-(poly(ethylene glycol)-CH2-CO-alaninyl)-4',6'-dimethylphenyl)-3,3-dimethylpropionic acid

3-(2'-(poly(ethylene glycol)-CH2-CO-alaninyl)-4',6'-dimethylphenyl)-3,3-dimethylpropionic acid

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

3-(2'-(poly(ethylene glycol)-CH2-CO-alaninyl)-4',6'-dimethylphenyl)-3,3-dimethylpropionic acid, amid with daunorubicin

3-(2'-(poly(ethylene glycol)-CH2-CO-alaninyl)-4',6'-dimethylphenyl)-3,3-dimethylpropionic acid, amid with daunorubicin

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Condensation;92%
daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

benzyl chloroformate
501-53-1

benzyl chloroformate

C35H35NO12

C35H35NO12

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 10h;92%
3-(2'-(poly(ethylene glycol)-CH2-CO-β-alaninyl)-4',6'-dimethylphenyl)-3,3-dimethylpropionic acid

3-(2'-(poly(ethylene glycol)-CH2-CO-β-alaninyl)-4',6'-dimethylphenyl)-3,3-dimethylpropionic acid

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

3-(2'-(poly(ethylene glycol)-CH2-CO-β-alaninyl)-4',6'-dimethylphenyl)-3,3-dimethylpropionic acid, amid with daunorubicin

3-(2'-(poly(ethylene glycol)-CH2-CO-β-alaninyl)-4',6'-dimethylphenyl)-3,3-dimethylpropionic acid, amid with daunorubicin

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Condensation;90%
3-(2'-(poly(ethylene glycol)-CH2-CO-alaninyl)-3',6'-dimethylphenyl)-3,3-dimethylpropionic acid

3-(2'-(poly(ethylene glycol)-CH2-CO-alaninyl)-3',6'-dimethylphenyl)-3,3-dimethylpropionic acid

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

3-(2'-(poly(ethylene glycol)-CH2-CO-alaninyl)-3',6'-dimethylphenyl)-3,3-dimethylpropionic acid, amid with daunorubicin

3-(2'-(poly(ethylene glycol)-CH2-CO-alaninyl)-3',6'-dimethylphenyl)-3,3-dimethylpropionic acid, amid with daunorubicin

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Condensation;90%
3-(2'-(poly(ethylene glycol)-CH2-CO-β-alaninyl)-3',6'-dimethylphenyl)-3,3-dimethylpropionic acid

3-(2'-(poly(ethylene glycol)-CH2-CO-β-alaninyl)-3',6'-dimethylphenyl)-3,3-dimethylpropionic acid

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

3-(2'-(poly(ethylene glycol)-CH2-CO-β-alaninyl)-3',6'-dimethylphenyl)-3,3-dimethylpropionic acid, amid daunorubicin

3-(2'-(poly(ethylene glycol)-CH2-CO-β-alaninyl)-3',6'-dimethylphenyl)-3,3-dimethylpropionic acid, amid daunorubicin

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Condensation;90%
3-(2'-(2''-(2''-poly(ethylene glycol)-CH2-CO-aminoethoxy)ethoxycarbonyloxy)-4',6'-dimethylphenyl)-3,3-dimethylpropionic acid

3-(2'-(2''-(2''-poly(ethylene glycol)-CH2-CO-aminoethoxy)ethoxycarbonyloxy)-4',6'-dimethylphenyl)-3,3-dimethylpropionic acid

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

3-(2'-(2''-(2''-poly(ethylene glycol)-CH2-CO-aminoethoxy)ethoxycarbonyloxy)-4',6'-dimethylphenyl)-3,3-dimethylpropionic acid, amid with daunorubicin

3-(2'-(2''-(2''-poly(ethylene glycol)-CH2-CO-aminoethoxy)ethoxycarbonyloxy)-4',6'-dimethylphenyl)-3,3-dimethylpropionic acid, amid with daunorubicin

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Condensation;90%
isoniazid
54-85-3

isoniazid

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

Isonicotinic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride
110925-39-8

Isonicotinic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride

Conditions
ConditionsYield
In methanol Heating;89%
daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

14-bromodaunorubicin hydrochloride
29742-67-4

14-bromodaunorubicin hydrochloride

Conditions
ConditionsYield
Stage #1: daunomycin hydrochloride With trimethyl orthoformate In 1,4-dioxane; methanol at 20℃; for 0.333333h;
Stage #2: With bromine In 1,4-dioxane; methanol; chloroform at 20℃; for 0.666667h; pH=7;
89%
Stage #1: daunomycin hydrochloride With trimethyl orthoformate In 1,4-dioxane; methanol at 20℃; for 0.333333h;
Stage #2: With bromine In 1,4-dioxane; methanol; chloroform at 30℃; for 0.666667h;
84%
daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

14-bromodaunorubicin

14-bromodaunorubicin

Conditions
ConditionsYield
With bromine; trimethyl orthoformate In 1,4-dioxane; methanol; chloroform at 20℃; for 1h;89%
daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

14-bromodaunorubicin
65026-79-1

14-bromodaunorubicin

Conditions
ConditionsYield
With bromine In 1,4-dioxane; methanol; chloroform for 2h; Ambient temperature;88%
Multi-step reaction with 2 steps
1: bromine; hydrogen bromide / methanol; 1,4-dioxane / 2 - 6 °C / Inert atmosphere
2: hydrogen bromide / acetone; water / 6 h / 15 - 20 °C / pH 3
View Scheme
daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

A

(2R)-2-acetyl-1,2,3,4-tetrahydro-2,11-dihydroxy-7-methoxy-5,12-naphthacenedione
98151-30-5

(2R)-2-acetyl-1,2,3,4-tetrahydro-2,11-dihydroxy-7-methoxy-5,12-naphthacenedione

B

(2R)-2-acetyl-1,2,3,4-tetrahydro-2,6-dihydroxy-7-methoxy-5,12-naphthacenedione
101810-85-9

(2R)-2-acetyl-1,2,3,4-tetrahydro-2,6-dihydroxy-7-methoxy-5,12-naphthacenedione

Conditions
ConditionsYield
Stage #1: daunomycin hydrochloride With hydrogen; Pd-BaSO4 In methanol at 20℃; for 5.5h; Catalytic hydrogenation;
Stage #2: With air In methanol Oxidation;
A 88%
B 8%
3-[2'-(poly(ethylene glycol)-CH2-CO-NH-(CH2-CH2-O)2-CH2-CH2-NH-CO-O)-4',6'-dimethylphenyl]-3,3-dimethylpropionic acid

3-[2'-(poly(ethylene glycol)-CH2-CO-NH-(CH2-CH2-O)2-CH2-CH2-NH-CO-O)-4',6'-dimethylphenyl]-3,3-dimethylpropionic acid

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

3-[2'-(poly(ethylene glycol)-CH2-CO-NH-(CH2-CH2O)2-CH2-CH2-NH-CO-O)-4',6'-dimethylphenyl]-3,3-dimethylpropionic acid, amid with daunorubicin

3-[2'-(poly(ethylene glycol)-CH2-CO-NH-(CH2-CH2O)2-CH2-CH2-NH-CO-O)-4',6'-dimethylphenyl]-3,3-dimethylpropionic acid, amid with daunorubicin

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Condensation;88%
daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

C35H37NO11

C35H37NO11

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 10h;88%
3-(2'-(poly(ethylene glycol)-CH2-CO-prolinyl)-4',6'-dimethylphenyl)-3,3-dimethylpropionic acid

3-(2'-(poly(ethylene glycol)-CH2-CO-prolinyl)-4',6'-dimethylphenyl)-3,3-dimethylpropionic acid

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

3-(2'-(poly(ethylene glycol)-CH2-CO-prolinyl)-4',6'-dimethylphenyl)-3,3-dimethylpropionic acid, amid with daunorubicin

3-(2'-(poly(ethylene glycol)-CH2-CO-prolinyl)-4',6'-dimethylphenyl)-3,3-dimethylpropionic acid, amid with daunorubicin

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Condensation;84%
daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

propargyl bromide
106-96-7

propargyl bromide

A

(8S,10S)-8-acetyl-6,8,11-trihydroxy-10-{[(2R,4S,5S,6S)-5-hydroxy-6-methyl-4-(di(prop-2-yn-1-yl)amino)tetrahydro-2H-pyran-2-yl]oxy}-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione

(8S,10S)-8-acetyl-6,8,11-trihydroxy-10-{[(2R,4S,5S,6S)-5-hydroxy-6-methyl-4-(di(prop-2-yn-1-yl)amino)tetrahydro-2H-pyran-2-yl]oxy}-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione

B

(8S,10S)-8-acetyl-6,8,11-trihydroxy-10-{[(2R,4S,5S,6S)-5-hydroxy-6-methyl-4-(prop-2-yn-1-ylamino)tetrahydro-2H-pyran-2-yl]oxy}-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione

(8S,10S)-8-acetyl-6,8,11-trihydroxy-10-{[(2R,4S,5S,6S)-5-hydroxy-6-methyl-4-(prop-2-yn-1-ylamino)tetrahydro-2H-pyran-2-yl]oxy}-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione

Conditions
ConditionsYield
With potassium carbonate In dichloromethane; N,N-dimethyl-formamide at 20℃;A 15%
B 81%
succinic acid anhydride
108-30-5

succinic acid anhydride

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

N-[(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)-3-hydroxy-2-methyl-tetrahydro-pyran-4-yl]-succinamic acid

N-[(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)-3-hydroxy-2-methyl-tetrahydro-pyran-4-yl]-succinamic acid

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 72h; Inert atmosphere; Darkness;80.8%
With triethylamine In N,N-dimethyl-formamide at 20℃; for 72h; Inert atmosphere; Darkness;80.8%

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