Maysine

Base Information

• Chemical Name: Maysine
• CAS No.: 52978-28-6
• Molecular Formula: C28H35ClN2O7
• Molecular Weight: 547.04
• Mol file: 52978-28-6.mol

Synonyms:MAYSINE;NSC 219972;(2E)-3-De(2-(acetylmethylamino)-1-oxopropoxy)-2,3-didehydromaytansine;Maytansine, 3-de(2-(acetylmethylamino)-1-oxopropoxy)-2,3-didehydro-, (2E)-;52978-28-6;C28H35ClN2O7;C28-H35-Cl-N2-O7

Chemical Property of Maysine

Chemical Property:

• Vapor Pressure: 6.59E-23mmHg at 25°C
• Boiling Point: 738.6°C at 760 mmHg
• Flash Point: 400.5°C
• PSA: 109.86000
• Density: 1.32g/cm³
• LogP: 4.31570
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 546.2132792
• Heavy Atom Count: 38
• Complexity: 1000

Purity/Quality:

99% ^*data from raw 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)C=CC4(C1O4)C)C)C)OC)(NC(=O)O2)O
• Isomeric SMILES: CC1C2CC(C(/C=C/C=C(/CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)/C=C\C4(C1O4)C)C)\C)OC)(NC(=O)O2)O

Technology Process of Maysine

There total 38 articles about Maysine 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:

phosgene (75-44-5) + (4E,14E,16E)-(6S,8S,9R,10S,13R)-22-Chloro-10-hydroxy-13,21-dimethoxy-2,6,9,17-tetramethyl-7-oxa-2-aza-tricyclo[17.3.1.06,8]tricosa-1(23),4,14,16,19,21-hexaene-3,12-dione (86116-99-6) → (-)-maysine (52978-28-6)

Guidance literature:

With pyridine; ammonia; In dichloromethane; toluene; at -78 ℃; for 2h;

DOI:10.1021/ja00353a027

Reference yield:

4-hydroxy-3-methoxybenzoic acid methyl ester (3943-74-6) → (-)-maysine (52978-28-6)

Guidance literature:

Multi-step reaction with 18 steps

1: 74 percent / HNO₃, glacial acetic acid / acetic acid / 2 h / Ambient temperature

2: 88 percent / oxalyl chloride / dimethylformamide / -20 deg C; 80 deg C, 3 h

3: 30 g / KOH / ethanol; H₂O / 2 h / 80 °C

4: 60 percent / mercuric oxide, bromine / CCl₄ / 5 h / Irradiation

5: 1.) iron, 2.) HCl / 1.) ethanol, water, 2.) reflux, 12 h

6: 67 percent / aniline, pyridine / CH₂Cl₂ / 1.) 0 deg C, 10 min; 2.) room temperature, 1 h

7: t-BuOK / tetrahydrofuran / Ambient temperature

8: 1.) t-BuOK / 1.) THF, 0 deg C, 30 min, 2.) room temperature

9: 1.) n-BuLi, 2.) pentynylcopper, hexamethylphoshpotriamide / 1.) THF, hexane, -110 deg C -> -78 deg C; -78 deg C, 1.5 h, 2.) -78 deg C, 2.5 h, 3.) -78 deg C, 4.5 h

10: tert-butyllithium / tetrahydrofuran; pentane / 1.) -120 deg C, 30 min, 2.) -120 deg C -> -95 deg C, 30 min

11: tetrahydrofuran; pentane / 1.) -120 deg C, 30 min, 2.) -78 deg C, 1 h

12: 1.) NaH / 1.) THF, -20 deg C, 15 min, 2.) -20 deg C, 10 min

13: tetrabutylammonium chloride / tetrahydrofuran / 1. ) 0 deg C, 30 min, 2.) room temperature, overnight

14: 1.) tert-butoxymagnesium bromide, 2.) 1,1'-(azodicarbonyl)dipiperidine / 1.) 0 deg C, 10 min, 2.) 0 deg C -> 18 deg C, 12 h

15: 83 percent / pyridine / CH₂Cl₂ / 1 h / Ambient temperature

16: 62 percent / potassium tert-butoxide / tetrahydrofuran / 1-) -120 deg C, 1 h, 2.) -120 deg C -> room temperature

17: 67 percent / calcium carbonate, mercuric chloride / acetonitrile / 3 h / Ambient temperature

18: 3 mg / ammonia, pyridine / CH₂Cl₂; toluene / 2 h / -78 °C

With pyridine; 1-pentynyl copper; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; n-butyllithium; oxalyl dichloride; potassium tert-butylate; tetrabutyl-ammonium chloride; ammonia; bromine; tert.-butyl lithium; nitric acid; t-BuOMgBr; iron; sodium hydride; acetic acid; aniline; calcium carbonate; mercury dichloride; mercury(II) oxide; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; toluene; acetonitrile; pentane;

DOI:10.1021/ja00353a027

Reference yield:

(3S,4R)-4-[(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-oxiranyl]-3-hydroxy-pentanedithioic acid ethyl ester (86116-92-9) → (-)-maysine (52978-28-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 81 percent / p-toluenesulfonic acid / diethyl ether / 1.) 0 deg C, 10 min, 2.) 25 deg C, 1 h

2: tetrahydrofuran / 2 h / -25 °C

3: 83 percent / tetrahydrofuran / 2 h / -25 °C

4: tetrahydrofuran; pentane / 1.) -120 deg C, 30 min, 2.) -78 deg C, 1 h

5: 1.) NaH / 1.) THF, -20 deg C, 15 min, 2.) -20 deg C, 10 min

6: tetrabutylammonium chloride / tetrahydrofuran / 1. ) 0 deg C, 30 min, 2.) room temperature, overnight

7: 1.) tert-butoxymagnesium bromide, 2.) 1,1'-(azodicarbonyl)dipiperidine / 1.) 0 deg C, 10 min, 2.) 0 deg C -> 18 deg C, 12 h

8: 83 percent / pyridine / CH₂Cl₂ / 1 h / Ambient temperature

9: 62 percent / potassium tert-butoxide / tetrahydrofuran / 1-) -120 deg C, 1 h, 2.) -120 deg C -> room temperature

10: 67 percent / calcium carbonate, mercuric chloride / acetonitrile / 3 h / Ambient temperature

11: 3 mg / ammonia, pyridine / CH₂Cl₂; toluene / 2 h / -78 °C

With pyridine; potassium tert-butylate; tetrabutyl-ammonium chloride; ammonia; t-BuOMgBr; sodium hydride; toluene-4-sulfonic acid; calcium carbonate; mercury dichloride; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; acetonitrile; pentane;

DOI:10.1021/ja00353a027

upstream raw materials:

(4E,13E,15E)-1⁶-chloro-6r,7t-epoxy-9t-hydroxy-1⁵,12ξ-dimethoxy-2,6,8c,16-tetramethyl-2-aza-1(1,3)-benzena-cycloheptadecaphane-4,13,15-triene-3,11-dione

phosgene

(4E,14E,16E)-(6S,8S,9R,10S,13R)-22-Chloro-10-hydroxy-13,21-dimethoxy-2,6,9,17-tetramethyl-7-oxa-2-aza-tricyclo[17.3.1.0^6,8]tricosa-1⁽²³⁾,4,14,16,19,21-hexaene-3,12-dione

4-hydroxy-3-methoxybenzoic acid methyl ester

Refernces