Antibiotics from Streptomyces coeruleorubidus

Base Information

• Chemical Name: Antibiotics from Streptomyces coeruleorubidus
• CAS No.: 56390-08-0
• Molecular Formula: C27H29NO10^.HCl
• Molecular Weight: 563.989
• European Community (EC) Number: 245-723-4
• NSC Number: 301724,257457,249333,83142,304419,82151
• UN Number: 2811
• NCI Thesaurus Code: C1583
• RXCUI: 81992
• ChEMBL ID: CHEMBL158918
• Mol file: 56390-08-0.mol

Synonyms:Cerubidine;Dauno Rubidomycine;Dauno-Rubidomycine;Daunoblastin;Daunoblastine;Daunomycin;Daunorubicin;Daunorubicin Hydrochloride;Hydrochloride, Daunorubicin;NSC 82151;NSC-82151;NSC82151;Rubidomycin;Rubomycin

Chemical Property of Antibiotics from Streptomyces coeruleorubidus

Chemical Property:

• Vapor Pressure: 6.99E-26mmHg at 25°C
• Boiling Point: 770 °C at 760 mmHg
• Flash Point: 419.5 °C
• PSA: 185.84000
• LogP: 2.53120
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 563.1558238
• Heavy Atom Count: 39
• Complexity: 960
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

(8S-CIS)-8-ACETYL-10-[(3-AMINO-2,3,6-TRIDEOXY-ALPHA-L-ARABINO-HEXOPYRANOSYL)OXY]-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-1-METHOXYNAPHTHACENE-5,12-DIONE HYDROCHLORIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)C)O)N)O.Cl
• Isomeric SMILES: CC1C(C(CC(O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)C)O)N)O.Cl
• Recent ClinicalTrials: Selinexor With Combination With Induction/Consolidation Therapy in Acute Myeloid Leukemia Patients
• Recent EU Clinical Trials: A Phase 1B/2 Study To Evaluate The Safety And Efficacy of PF-04449913, An Oral Hedgehog Inhibitor, In Combination With Intensive Chemotherapy, Low Dose ARA-C Or Decitabine In Patients With Acute Myeloid Leukemia Or High-Risk Myelodysplastic Syndrome
• Uses: Daunorubicin (D194500) impurity. Daunomycin analog antitumor.

Technology Process of Antibiotics from Streptomyces coeruleorubidus

There total 14 articles about Antibiotics from Streptomyces coeruleorubidus which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

4'-epi-N-(trifluoroacetyl)daunorubicin (57918-22-6,52471-41-7,64686-33-5) → chlorhydrate de 3,4-diepidaunorubicine (56390-08-0)

Guidance literature:

4'-epi-N-(trifluoroacetyl)daunorubicin; With sodium hydroxide; water; at 30 ℃; for 0.5h;

With hydrogenchloride; water; pH=7;

Reference yield:

1,5-anhydro-3,4-di-O-benzoyl-2,6-didesoxy-L-arabino-hex-1-enitol (34820-21-8) → chlorhydrate de 3,4-diepidaunorubicine (56390-08-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NaN₃; 2.) LiAlH₄ / 1.) DMF, 140 deg C, 2.5 h; 2.) ether, 0 deg C, 15 min

2: 95 percent / triethylamine / CH₂Cl₂ / 0.08 h / 20 °C

3: 100 percent / pyridine / 16 h / 20 °C

4: 41 percent / TsOH / benzene; CH₂Cl₂ / 2 h / Heating

5: 1.) 0.1M aq. NaOH; 2.) HCl / 1.) dioxane, 20 deg C, 1h; 2.) dichloromethane

With hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; sodium azide; toluene-4-sulfonic acid; triethylamine; In pyridine; dichloromethane; benzene;

DOI:10.1016/S0008-6215(00)83831-8

Reference yield:

2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-(trifluoroacetamido)-L-ribo-hex-1-enitol (73891-07-3) → chlorhydrate de 3,4-diepidaunorubicine (56390-08-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 41 percent / TsOH / benzene; CH₂Cl₂ / 2 h / Heating

2: 1.) 0.1M aq. NaOH; 2.) HCl / 1.) dioxane, 20 deg C, 1h; 2.) dichloromethane

With hydrogenchloride; sodium hydroxide; toluene-4-sulfonic acid; In dichloromethane; benzene;

DOI:10.1016/S0008-6215(00)83831-8

upstream raw materials:

(+)-Daunomycinone

acetic anhydride

2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-D-lyxo-hexopyranose

methyl-3-acetamido-2,3,6-tridesoxy-α-D-lyxo-hexopyranoside

Downstream raw materials:

C₂₇H₂₈BrNO₁₀

C₂₇H₂₈BrNO₁₀*ClH

Refernces

• 1、 -. "Process for the preparation of 4'-epidaunorubicin, 3',4'-diepidaunorubicin, their doxorubicin analogs, and intermediates used in said process". . . Retrieved 2008/06/13.
• 2、 Boivin, J.,Pais, M.,Monneret, C.. "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". . p. 193 - 204. Retrieved 2007/10/02.