[(1S,2R,3S,5R,6S,16E,18E,20R,21S)-11-Chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] (2S)-2-[acetyl(methyl)amino]propanoate

Base Information

• Chemical Name: [(1S,2R,3S,5R,6S,16E,18E,20R,21S)-11-Chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] (2S)-2-[acetyl(methyl)amino]propanoate
• CAS No.: 35846-53-8
• Molecular Formula: C34H46 Cl N3 O10
• Molecular Weight: 692.206
• European Community (EC) Number: 252-754-7
• Metabolomics Workbench ID: 21289
• NCI Thesaurus Code: C626
• 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 [(1S,2R,3S,5R,6S,16E,18E,20R,21S)-11-Chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] (2S)-2-[acetyl(methyl)amino]propanoate

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% ^*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
• General Description: **Null**

Technology Process of [(1S,2R,3S,5R,6S,16E,18E,20R,21S)-11-Chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] (2S)-2-[acetyl(methyl)amino]propanoate

There total 11 articles about [(1S,2R,3S,5R,6S,16E,18E,20R,21S)-11-Chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] (2S)-2-[acetyl(methyl)amino]propanoate 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

SYNTHETIC STUDIES TOWARD MAYTANSINOIDS. PREPARATION OF THE OPTICALLY ACTIVE INTERMEDIATES FROM D-MANNOSE

10.1246/cl.1981.457

The research focuses on the synthetic studies toward maytansinoids, specifically the preparation of optically active intermediates (15 and 23) from D-mannose. The purpose of this study was to develop a new synthetic strategy for maytansine, a naturally occurring anti-cancer agent, by utilizing D-mannose as a chiral starting material. The researchers synthesized the intermediates through a series of chemical reactions, with a crucial step involving heteroconjugate addition of methyllithium.