Maytansine

Base Information

• Chemical Name: Maytansine
• CAS No.: 35846-53-8
• Molecular Formula: C34H46 Cl N3 O10
• Molecular Weight: 692.206
• European Community (EC) Number: 252-754-7
• UNII: 14083FR882
• ChEMBL ID: CHEMBL292702
• DSSTox Substance ID: DTXSID00879995
• Metabolomics Workbench ID: 21289
• NCI Thesaurus Code: C626
• Wikidata: Q6720157
• Wikipedia: Maitansine
• Mol file: 35846-53-8.mol

Synonyms:DM1, Maytansinoid;DM4, Maytansinoid;DMMO Maytansine;DMMO-maytansine;emtansine;Maitansine;Maytansine;Maytansinoid DM1;Maytansinoid DM4;Mertansine;N2'-deacetyl-N2'-(4-mercapto-4-methyl-1-oxopentyl)maytansine;Ravtansine;Soravtansine

Chemical Property of Maytansine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 183.5-184℃
• Refractive Index: 1.59
• Boiling Point: 895.1°Cat760mmHg
• PKA: 9.82±0.70(Predicted)
• Flash Point: 495.1°C
• PSA: 156.47000
• Density: 1.32g/cm³
• LogP: 3.92820
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 691.2871724
• Heavy Atom Count: 48
• Complexity: 1300

Purity/Quality:

99%min ^*data from raw suppliers

Maytansine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CC(C(C=CC=C(CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)CC(C4(C1O4)C)OC(=O)C(C)N(C)C(=O)C)C)C)OC)(NC(=O)O2)O
• Isomeric SMILES: C[C@@H]1[C@@H]2C[C@]([C@@H](/C=C/C=C(/CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)C[C@@H]([C@]4([C@H]1O4)C)OC(=O)[C@H](C)N(C)C(=O)C)C)\C)OC)(NC(=O)O2)O
• Description: This novel ansa macrolide alkaloid occurs in a number of May tan us species. The structure given has been elucidated from chemical and spectroscopic data. In low doses (25-50 mcg/kg), maytansine prolonged the survival of mice bearing vincristine-sensitive P388 leukemia but not those bearing vincristine-resistant tumour lines. In vitro, it suppressed the growth of U21 0, LSl78Y and P388 leukemia cells with ED50 of 2 X 10-9 , 1.5 X 10-9 and 6 X 10-10M respectively and elevated the mitotic index in L 121 0 cells. From labelling studies it was shown that the alkaloid inhibited DNA formation by P388 cells to a greater extent than RNA and protein synthesis. Maytensine did not inhibit RNA polymerase from Escherichia coli at levels as high as 1 X 10-4M.
• Uses: Antineoplastic.
• Biological Functions: Maytansine is a potent microtubule-targeted compound that inhibits proliferation of cells at mitosis. Antibody-maytansinoid conjugates consisting of maytansinoids (DM1 and DM4) attached to tumor-specific antibodies have shown promising clinical results The microtubule-targeting maytansinoids accumulate in cells and induce mitotic arrest at 250- to 1000-fold lower concentrations than those required for their association with tubulin or microtubules.

Technology Process of Maytansine

There total 11 articles about Maytansine 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: 95.0%

maytansine 9-O-methyl ether (64817-73-8) → maytansine (35846-53-8)

Guidance literature:

With pyridine hydrochloride; In tetrahydrofuran; at 25 ℃; for 14h;

DOI:10.1021/ja00541a064

Reference yield:

4-deoxymaytansinol (75340-67-9) → maytansine (35846-53-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 0.1 percent p-toluenesulfonic acid / 0.5 h / 25 °C

2: 87 percent / tert-butyl hydroperoxide, oxyvanadium(IV) bis(acetylacetonate), 2,6-lutidine / benzene; toluene / 3.5 h / 25 °C

3: imidazole / dimethylformamide; 1,2-dimethoxy-ethane / 75 h / 45 - 47 °C

4: 95 percent / aq. pyridinium chloride / tetrahydrofuran / 14 h / 25 °C

With 1H-imidazole; 2,6-dimethylpyridine; tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; pyridine hydrochloride; toluene-4-sulfonic acid; In tetrahydrofuran; 1,2-dimethoxyethane; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/ja00541a064

Reference yield:

(3E,5E,14E)-(7R,8S,12S,13S,16S)-21-Chloro-16-hydroxy-7,8,22-trimethoxy-3,13,15,19-tetramethyl-11-oxa-9,19-diaza-tricyclo[18.3.1.18,12]pentacosa-1(24),3,5,14,20,22-hexaene-10,18-dione (75349-70-1) → maytansine (35846-53-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / tert-butyl hydroperoxide, oxyvanadium(IV) bis(acetylacetonate), 2,6-lutidine / benzene; toluene / 3.5 h / 25 °C

2: imidazole / dimethylformamide; 1,2-dimethoxy-ethane / 75 h / 45 - 47 °C

3: 95 percent / aq. pyridinium chloride / tetrahydrofuran / 14 h / 25 °C

With 1H-imidazole; 2,6-dimethylpyridine; tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; pyridine hydrochloride; In tetrahydrofuran; 1,2-dimethoxyethane; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/ja00541a064

upstream raw materials:

maytansine 9-O-methyl ether

4-deoxymaytansinol

(3E,5E,14E)-(7R,8S,12S,13S,16S)-21-Chloro-16-hydroxy-7,8,22-trimethoxy-3,13,15,19-tetramethyl-11-oxa-9,19-diaza-tricyclo[18.3.1.1^8,12]pentacosa-1⁽²⁴⁾,3,5,14,20,22-hexaene-10,18-dione

C₃₆H₅₆ClNO₅S₂Si

Downstream raw materials:

Maysin

Refernces