{2-Chloro-3-methoxy-5-[(E)-2-methyl-5-((S)-toluene-4-sulfinyl)-pent-2-enyl]-phenyl}-methyl-carbamic acid methyl ester

Base Information

• Chemical Name: {2-Chloro-3-methoxy-5-[(E)-2-methyl-5-((S)-toluene-4-sulfinyl)-pent-2-enyl]-phenyl}-methyl-carbamic acid methyl ester
• CAS No.: 180865-96-7
• Molecular Formula: C₂₃H₂₈ClNO₄S
• Molecular Weight: 449.999
• Mol file: 180865-96-7.mol

Synonyms:{2-Chloro-3-methoxy-5-[(E)-2-methyl-5-((S)-toluene-4-sulfinyl)-pent-2-enyl]-phenyl}-methyl-carbamic acid methyl ester

Chemical Property of {2-Chloro-3-methoxy-5-[(E)-2-methyl-5-((S)-toluene-4-sulfinyl)-pent-2-enyl]-phenyl}-methyl-carbamic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {2-Chloro-3-methoxy-5-[(E)-2-methyl-5-((S)-toluene-4-sulfinyl)-pent-2-enyl]-phenyl}-methyl-carbamic acid methyl ester

There total 1 articles about {2-Chloro-3-methoxy-5-[(E)-2-methyl-5-((S)-toluene-4-sulfinyl)-pent-2-enyl]-phenyl}-methyl-carbamic acid methyl ester 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:

(S)-methyl p-tolyl sulfoxide (5056-07-5) + [5-((E)-4-Bromo-2-methyl-but-2-enyl)-2-chloro-3-methoxy-phenyl]-methyl-carbamic acid methyl ester (74510-49-9) → {2-Chloro-3-methoxy-5-[(E)-2-methyl-5-((S)-toluene-4-sulfinyl)-pent-2-enyl]-phenyl}-methyl-carbamic acid methyl ester (180865-96-7)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction; 1) THF, hexane, HMPA, -78 deg C, 10 min; 2) THF, hexane, HMPA, -78 - -20 deg C, 90 min;

DOI:10.1021/jo960363a

Reference yield: 55.0%

{2-Chloro-3-methoxy-5-[(E)-2-methyl-5-((S)-toluene-4-sulfinyl)-pent-2-enyl]-phenyl}-methyl-carbamic acid methyl ester (180865-96-7) + 2-[(E)-(2S,3S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-8,8-diethoxy-2-(2-methoxy-ethoxymethoxy)-3,5-dimethyl-oct-4-enyl]-[1,3]dithiane-2-carbaldehyde (1026598-10-6) → C45H76ClNO10S2Si (1053627-73-8) + C45H76ClNO10S2Si

Guidance literature:

With lithium diisopropyl amide; In 1,2-dimethoxyethane; n-heptane; at -78 ℃; for 3h; Yields of byproduct given;

DOI:10.1021/jo960363a

Reference yield:

{2-Chloro-3-methoxy-5-[(E)-2-methyl-5-((S)-toluene-4-sulfinyl)-pent-2-enyl]-phenyl}-methyl-carbamic acid methyl ester (180865-96-7) → (-)-maytansinol (57103-68-1,75494-64-3,75520-30-8,75520-31-9,75520-32-0,93221-26-2,109904-94-1)

Guidance literature:

Multi-step reaction with 13 steps

1: 55 percent / LDA / 1,2-dimethoxy-ethane; heptane / 3 h / -78 °C

2: 98 percent / Ag₂O / ethyl acetate / 1.5 h / 60 °C

3: 86 percent / tetrabutyl ammonium fluoride / tetrahydrofuran / 48 h / 50 °C

4: 54 percent / aq. HCl / tetrahydrofuran / 2 h / Ambient temperature

5: 78 percent / DBU / CH₂Cl₂ / 18 h / Ambient temperature

6: 72 percent / DIBAH / toluene / -78 - -60 °C

7: 66 percent / tri-n-butylamine, 2-chloro-1-methylpyridinium iodide / CH₂Cl₂ / 16 h / 32 °C

8: 53 percent / 2-chloro-1,3,2-dithioborolane / CH₂Cl₂ / 2 h / -60 °C

9: pyridine / CH₂Cl₂ / 24 h / Ambient temperature

10: NH₃ / methanol / 14 h / Ambient temperature

11: CaCO₃, HgCl₂ / acetonitrile; H₂O / 18 h / Ambient temperature

12: aq. HF / 2 h / Ambient temperature

13: 45 percent / 2,6-lutidine, t-BuOOH, VO(aca)2 / toluene / 24 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; tributyl-amine; hydrogen fluoride; tetrabutyl ammonium fluoride; 2-chloro-1-methyl-pyridinium iodide; ammonia; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; calcium carbonate; mercury dichloride; silver(l) oxide; lithium diisopropyl amide; 2-chloro-1,3,2-dithioborolane; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; n-heptane; dichloromethane; water; ethyl acetate; toluene; acetonitrile;

DOI:10.1021/jo960363a

upstream raw materials:

(S)-methyl p-tolyl sulfoxide

[5-((E)-4-Bromo-2-methyl-but-2-enyl)-2-chloro-3-methoxy-phenyl]-methyl-carbamic acid methyl ester

Downstream raw materials:

C₄₅H₇₆ClNO₁₀S₂Si

(-)-maytansinol

(E)-(3S,6S,7S)-8-(2-{(2E,4E)-(R)-6-[4-Chloro-3-methoxy-5-(methoxycarbonyl-methyl-amino)-phenyl]-1-methoxy-5-methyl-hexa-2,4-dienyl}-[1,3]dithian-2-yl)-3-hydroxy-7-(2-methoxy-ethoxymethoxy)-4,6-dimethyl-oct-4-enoic acid

(E)-(3S,6S,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-8-{2-[(2E,4E)-(R)-6-(4-chloro-3-methoxy-5-methylamino-phenyl)-1-methoxy-5-methyl-hexa-2,4-dienyl]-[1,3]dithian-2-yl}-7-(2-methoxy-ethoxymethoxy)-4,6-dimethyl-oct-4-enoic acid