N2'-Deacetyl-N2'-(4-mercapto-4-methyl-1-oxopentyl)-maytansine

Base Information

• Chemical Name: N2'-Deacetyl-N2'-(4-mercapto-4-methyl-1-oxopentyl)-maytansine
• CAS No.: 796073-69-3
• Deprecated CAS: 1194029-15-6
• Molecular Formula: C38H54ClN3O10S
• Molecular Weight: 780.38
• European Community (EC) Number: 641-067-1
• UNII: WOB38VS2NI
• NCI Thesaurus Code: C136538
• Mol file: 796073-69-3.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 N2'-Deacetyl-N2'-(4-mercapto-4-methyl-1-oxopentyl)-maytansine

Chemical Property:

• Melting Point: 185-187 °C (decomp)
• Boiling Point: 943.2±65.0 °C(Predicted)
• PKA: 9.82±0.70(Predicted)
• PSA: 195.27000
• Density: 1.29±0.1 g/cm3(Predicted)
• LogP: 5.39690
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 9
• Exact Mass: 779.3218438
• Heavy Atom Count: 53
• Complexity: 1430

Purity/Quality:

99%min ^*data from raw suppliers

N2''-Deacetyl-N2''-(4-mercapto-4-methyl-1-oxopentyl)-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)CCC(C)(C)S)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)CCC(C)(C)S)C)\C)OC)(NC(=O)O2)O
• Description: Ravtansine (DM4) is a maytansinoid, a chemical derivative of maytansine being investigated as the cytotoxic payload of a number of antibody-drug conjugates (ADCs).M4 is is an antitubulin agent that inhibit cell division. DM4 can be used in the preparation of antibody drug conjugate.
• Uses: N2''-Deacetyl-N2''-(4-mercapto-4-methyl-1-oxopentyl)-maytansine is an intermediate used to prepare semisynthetic maytansine analogs which can be conjugated with antibodies for the targeted treatment of cancer.

Technology Process of N2'-Deacetyl-N2'-(4-mercapto-4-methyl-1-oxopentyl)-maytansine

There total 8 articles about N2'-Deacetyl-N2'-(4-mercapto-4-methyl-1-oxopentyl)-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: 97.0%

N2'-deacetyl-N2'-[4-methyl-4-(methyldithio)-1-oxopentyl]maytansine (796073-68-2) → N2′-deacetyl-N2′-(4-mercapto-4-methyl-1-oxopentyl)maytansine (796073-69-3)

Guidance literature:

With diothiothreitol; In methanol; phosphate buffer; ethyl acetate; for 3h; pH=7.5;

DOI:10.1021/jm060319f

Reference yield:

N-methyl-N-(4-methyldithio-4-methyl-1-oxopentyl)-L-alanine anhydride + maytansinol (57103-68-1) → N2′-deacetyl-N2′-(4-mercapto-4-methyl-1-oxopentyl)maytansine (796073-69-3)

Guidance literature:

With bis(bis(trimethylsilyl)amido)zinc(II); In dichloromethane; at 20 ℃;

Reference yield:

4-mercapto-4-methylvaleronitrile (131237-84-8) → N2′-deacetyl-N2′-(4-mercapto-4-methyl-1-oxopentyl)maytansine (796073-69-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 10 g / aq. NaOH / ethanol / Heating

2: 70 percent / sodium carbonate / ethanol; H₂O / 3 h / 20 °C

3: 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl / CH₂Cl₂ / 2 h

4: triethylamine / H₂O; 1,2-dimethoxy-ethane / 2 h

5: 36 percent / dicyclohexylcarbodiimide; ZnCl₂ / CH₂Cl₂; diethyl ether / 2 h / 20 °C

6: 97 percent / dithiothreitol / methanol; ethyl acetate; aq. phosphate buffer / 3 h / pH 7.5

With sodium hydroxide; sodium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; zinc(II) chloride; diothiothreitol; In methanol; 1,2-dimethoxyethane; phosphate buffer; diethyl ether; ethanol; dichloromethane; water; ethyl acetate;

DOI:10.1021/jm060319f

upstream raw materials:

N^2'-deacetyl-N^2'-[4-methyl-4-(methyldithio)-1-oxopentyl]maytansine

4-mercapto-4-methylvaleronitrile

N-methyl-N-[4-methyl-(4-methyldithio)-1-oxopropyl]-L-alanine

N-methyl-N-[4-methyl-(4-methyldithio)-1-oxopentyl]-L-alanine

Downstream raw materials:

N²'-deacetyl-N²'-(4-methyl-4-methythio-1-oxopentyl)maytansine

Refernces

• 1、 -. "Uses of immunoconjugates targeting CD138". Sheet 3. . Retrieved 2016/04/20.
• 2、 Widdison, Wayne C.,Wilhelm, Sharon D.,Cavanagh, Emily E.,Whiteman, Kathleen R.,Leece, Barbara A.,Kovtun, Yelena,Goldmacher, Victor S.,Xie, Hongsheng,Steeves, Rita M.,Lutz, Robert J.,Zhao, Robert,Wang, Lintao,Bl?ttler, Walter A.,Chari, Ravi V. J.. "Semisynthetic Maytansine analogues for the targeted treatment of cancer". . p. 4392 - 4408. Retrieved 2007/10/03.