N-{2-Chloro-5-[(2E,4E)-(9R,10S)-9-(1-ethoxy-ethoxy)-7,7-bis-ethylsulfanyl-10-((2R,3S)-3-formyl-3-methyl-oxiranyl)-6-methoxy-2-methyl-undeca-2,4-dienyl]-3-methoxy-phenyl}-N-methyl-acetamide

Base Information Edit

Chemical Name:N-{2-Chloro-5-[(2E,4E)-(9R,10S)-9-(1-ethoxy-ethoxy)-7,7-bis-ethylsulfanyl-10-((2R,3S)-3-formyl-3-methyl-oxiranyl)-6-methoxy-2-methyl-undeca-2,4-dienyl]-3-methoxy-phenyl}-N-methyl-acetamide
CAS No.:75494-73-4
Molecular Formula:C₃₅H₅₄ClNO₇S₂
Molecular Weight:700.401
Hs Code.:
Mol file:75494-73-4.mol

N-{2-Chloro-5-[(2E,4E)-(9R,10S)-9-(1-ethoxy-ethoxy)-7,7-bis-ethylsulfanyl-10-((2R,3S)-3-formyl-3-methyl-oxiranyl)-6-methoxy-2-methyl-undeca-2,4-dienyl]-3-methoxy-phenyl}-N-methyl-acetamide

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Chemical Property of N-{2-Chloro-5-[(2E,4E)-(9R,10S)-9-(1-ethoxy-ethoxy)-7,7-bis-ethylsulfanyl-10-((2R,3S)-3-formyl-3-methyl-oxiranyl)-6-methoxy-2-methyl-undeca-2,4-dienyl]-3-methoxy-phenyl}-N-methyl-acetamide Edit

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Technology Process of N-{2-Chloro-5-[(2E,4E)-(9R,10S)-9-(1-ethoxy-ethoxy)-7,7-bis-ethylsulfanyl-10-((2R,3S)-3-formyl-3-methyl-oxiranyl)-6-methoxy-2-methyl-undeca-2,4-dienyl]-3-methoxy-phenyl}-N-methyl-acetamide

There total 1 articles about N-{2-Chloro-5-[(2E,4E)-(9R,10S)-9-(1-ethoxy-ethoxy)-7,7-bis-ethylsulfanyl-10-((2R,3S)-3-formyl-3-methyl-oxiranyl)-6-methoxy-2-methyl-undeca-2,4-dienyl]-3-methoxy-phenyl}-N-methyl-acetamide 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%

: 72729-17-0,72777-48-1,72777-49-2,72777-50-5,86117-46-6
(2R,3S)-3-[(6E,8E)-(1R,2S)-10-(4-Chloro-3-methoxy-5-methylamino-phenyl)-2-(1-ethoxy-ethoxy)-4,4-bis-ethylsulfanyl-5-methoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxirane-2-carbaldehyde

: 75-36-5
acetyl chloride

: 75448-83-8,75494-72-3,75494-73-4,75494-74-5
N-{2-Chloro-5-[(2E,4E)-(9R,10S)-9-(1-ethoxy-ethoxy)-7,7-bis-ethylsulfanyl-10-((2R,3S)-3-formyl-3-methyl-oxiranyl)-6-methoxy-2-methyl-undeca-2,4-dienyl]-3-methoxy-phenyl}-N-methyl-acetamide

Guidance literature:: With pyridine; at 0 ℃; for 3h;
DOI:10.1021/ja00541a054

Reference yield:

: 75448-83-8,75494-72-3,75494-73-4,75494-74-5
N-{2-Chloro-5-[(2E,4E)-(9R,10S)-9-(1-ethoxy-ethoxy)-7,7-bis-ethylsulfanyl-10-((2R,3S)-3-formyl-3-methyl-oxiranyl)-6-methoxy-2-methyl-undeca-2,4-dienyl]-3-methoxy-phenyl}-N-methyl-acetamide

: 57103-68-1
(+/-)-maytansinol

Guidance literature:: Multi-step reaction with 8 steps

1: AgNO₃, aq. NaOH / tetrahydrofuran / 2 h / 25 °C

2: diethyl ether / 0 °C

3: 56 percent / lithium (hexamethylsilyl)amide / tetrahydrofuran / 4 h / -78 °C

4: 98 percent / HgCl₂, aq. CaCO₃ / acetonitrile / 1.5 h / 25 °C

5: 1.0 N HCl / tetrahydrofuran / 2 h / 0 °C

6: pyridine / diethyl ether; tetrahydrofuran / 1 h / 0 °C

7: 55 percent / ammonia / tetrahydrofuran / -78 °C

8: 45 percent / sodium borohydride / tetrahydrofuran; methanol / 0.5 h / -40 °C

With pyridine; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; ammonia; silver nitrate; calcium carbonate; mercury dichloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; acetonitrile;
DOI:10.1021/ja00541a054