(2R,3S)-3-[(6E,8E)-(1R,2S,5R)-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

Base Information

Chemical Name:(2R,3S)-3-[(6E,8E)-(1R,2S,5R)-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
CAS No.:86117-46-6
Molecular Formula:C₃₃H₅₂ClNO₆S₂
Molecular Weight:658.364
Hs Code.:

(2R,3S)-3-[(6E,8E)-(1R,2S,5R)-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

Synonyms:(2R,3S)-3-[(6E,8E)-(1R,2S,5R)-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

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Chemical Property of (2R,3S)-3-[(6E,8E)-(1R,2S,5R)-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

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Technology Process of (2R,3S)-3-[(6E,8E)-(1R,2S,5R)-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

There total 27 articles about (2R,3S)-3-[(6E,8E)-(1R,2S,5R)-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 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:

: 3943-74-6
4-hydroxy-3-methoxybenzoic acid methyl ester

: 86117-46-6
(2R,3S)-3-[(6E,8E)-(1R,2S,5R)-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

Guidance literature:: Multi-step reaction with 14 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

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; bromine; tert.-butyl lithium; nitric acid; t-BuOMgBr; iron; sodium hydride; acetic acid; aniline; mercury(II) oxide; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ja00353a027

Reference yield:

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

: 86117-46-6
(2R,3S)-3-[(6E,8E)-(1R,2S,5R)-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

Guidance literature:: Multi-step reaction with 7 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

With tetrabutyl-ammonium chloride; t-BuOMgBr; sodium hydride; toluene-4-sulfonic acid; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; diethyl ether; pentane;
DOI:10.1021/ja00353a027

Reference yield:

: 86116-91-8
(2R,3S,4S)-(+)-5-tert-butyldimethylsilyloxy-3,4-epoxy-2,4-dimethylpentanal

: 86117-46-6
(2R,3S)-3-[(6E,8E)-(1R,2S,5R)-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

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) lithium diisopropylamide / 1.) THF, -78 deg c, 30 min, 2.) -120 deg C, 6 h

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

3: tetrahydrofuran / 2 h / -25 °C

4: 83 percent / tetrahydrofuran / 2 h / -25 °C

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

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

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

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

With tetrabutyl-ammonium chloride; t-BuOMgBr; sodium hydride; toluene-4-sulfonic acid; 1,1'-azodicarbonyl-dipiperidine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; pentane;
DOI:10.1021/ja00353a027