(E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-16-((E)-(R)-1-methyl-3-phenyl-allyl)-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,9,12-trione

Base Information

Chemical Name:(E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-16-((E)-(R)-1-methyl-3-phenyl-allyl)-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,9,12-trione
CAS No.:195818-26-9
Molecular Formula:C₃₆H₄₇ClN₂O₆
Molecular Weight:639.232
Hs Code.:

(E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-16-((E)-(R)-1-methyl-3-phenyl-allyl)-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,9,12-trione

Synonyms:(E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-16-((E)-(R)-1-methyl-3-phenyl-allyl)-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,9,12-trione

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Chemical Property of (E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-16-((E)-(R)-1-methyl-3-phenyl-allyl)-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,9,12-trione

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Technology Process of (E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-16-((E)-(R)-1-methyl-3-phenyl-allyl)-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,9,12-trione

There total 9 articles about (E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-16-((E)-(R)-1-methyl-3-phenyl-allyl)-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,9,12-trione 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: 47.0%

: 1026309-69-2
(S)-2-(3-Amino-2,2-dimethyl-propoxy)-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-1-carboxy-2-(3-chloro-4-methoxy-phenyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester

: 195818-26-9
(E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-16-((E)-(R)-1-methyl-3-phenyl-allyl)-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,9,12-trione

Guidance literature:: With pentafluorophenyl diphenyl-phosphinate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 4h; Ambient temperature;
DOI:10.1021/jo980536r

Reference yield:

: 26734-09-8
3-amino-2,2-dimethylpropan-1-ol

: 195818-26-9
(E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-16-((E)-(R)-1-methyl-3-phenyl-allyl)-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,9,12-trione

Guidance literature:: Multi-step reaction with 9 steps

1: 15.0 g / Et₃N, (dimethylamino)pyridine / CH₂Cl₂ / 1.) 0 to 25 deg C, 1 h, 2.) 25 deg, 18 h

2: 1.) hydroxybenzotriazole, 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide / 1.) CH₂Cl₂, 0 deg C, 1.5 h, 2.) CH₂Cl₂, 0 deg C, 2 h

3: 79 percent / BF₃*OEt₂ / CH₂Cl₂ / 2 h / 25 °C

4: 52 percent / NaH / tetrahydrofuran / 1 h / -78 - 25 °C

5: 70 percent / 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 2 h / 25 °C

6: 79 percent / aq. H₂O₂, LiOH hydrate / tetrahydrofuran / 0.5 h / 5 - 25 °C

7: 1.) 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide, (dimethylamino)pyridine / 1.) CH₂Cl₂, 25 deg C, 30 min, 2.) CH₂Cl₂, 15 min

8: 1.) Zn dust, AcOH, 2.) CF₃COOH / 1.) sonication, 45 min, then room temp., 30 min, 2.) room temp., 2 h

9: 47 percent / diisopropylethylamine, pentafluorophenyl diphenylphosphinate / dimethylformamide / 4 h / Ambient temperature

With dmap; lithium hydroxide; boron trifluoride diethyl etherate; pentafluorophenyl diphenyl-phosphinate; dihydrogen peroxide; sodium hydride; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo980536r

Reference yield:

: 175721-97-8
3-(tert-butyldimethylsilanyloxy)-2,2-dimethylpropylamine

: 195818-26-9
(E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-16-((E)-(R)-1-methyl-3-phenyl-allyl)-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,9,12-trione

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) hydroxybenzotriazole, 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide / 1.) CH₂Cl₂, 0 deg C, 1.5 h, 2.) CH₂Cl₂, 0 deg C, 2 h

2: 79 percent / BF₃*OEt₂ / CH₂Cl₂ / 2 h / 25 °C

3: 52 percent / NaH / tetrahydrofuran / 1 h / -78 - 25 °C

4: 70 percent / 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 2 h / 25 °C

5: 79 percent / aq. H₂O₂, LiOH hydrate / tetrahydrofuran / 0.5 h / 5 - 25 °C

6: 1.) 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide, (dimethylamino)pyridine / 1.) CH₂Cl₂, 25 deg C, 30 min, 2.) CH₂Cl₂, 15 min

7: 1.) Zn dust, AcOH, 2.) CF₃COOH / 1.) sonication, 45 min, then room temp., 30 min, 2.) room temp., 2 h

8: 47 percent / diisopropylethylamine, pentafluorophenyl diphenylphosphinate / dimethylformamide / 4 h / Ambient temperature

With dmap; lithium hydroxide; boron trifluoride diethyl etherate; pentafluorophenyl diphenyl-phosphinate; dihydrogen peroxide; sodium hydride; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo980536r