4-(3-{(S)-1-[(E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-2,5,9,12-tetraoxo-1,4-dioxa-8,11-diaza-cyclohexadec-13-en-16-yl]-ethyl}-oxiranyl)-benzoic acid methyl ester

Base Information

Chemical Name:4-(3-{(S)-1-[(E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-2,5,9,12-tetraoxo-1,4-dioxa-8,11-diaza-cyclohexadec-13-en-16-yl]-ethyl}-oxiranyl)-benzoic acid methyl ester
CAS No.:204398-12-9
Molecular Formula:C₃₈H₄₇ClN₂O₁₀
Molecular Weight:727.252
Hs Code.:

4-(3-{(S)-1-[(E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-2,5,9,12-tetraoxo-1,4-dioxa-8,11-diaza-cyclohexadec-13-en-16-yl]-ethyl}-oxiranyl)-benzoic acid methyl ester

Synonyms:4-(3-{(S)-1-[(E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-2,5,9,12-tetraoxo-1,4-dioxa-8,11-diaza-cyclohexadec-13-en-16-yl]-ethyl}-oxiranyl)-benzoic acid methyl ester

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Chemical Property of 4-(3-{(S)-1-[(E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-2,5,9,12-tetraoxo-1,4-dioxa-8,11-diaza-cyclohexadec-13-en-16-yl]-ethyl}-oxiranyl)-benzoic acid methyl ester

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Technology Process of 4-(3-{(S)-1-[(E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-2,5,9,12-tetraoxo-1,4-dioxa-8,11-diaza-cyclohexadec-13-en-16-yl]-ethyl}-oxiranyl)-benzoic acid methyl ester

There total 5 articles about 4-(3-{(S)-1-[(E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-2,5,9,12-tetraoxo-1,4-dioxa-8,11-diaza-cyclohexadec-13-en-16-yl]-ethyl}-oxiranyl)-benzoic 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: 33.0%

: 204398-11-8
cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-5-hydroxy-8-[4-(methoxycarbonyl)phenyl]-6-methyl-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl]

: 204398-12-9
4-(3-{(S)-1-[(E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-2,5,9,12-tetraoxo-1,4-dioxa-8,11-diaza-cyclohexadec-13-en-16-yl]-ethyl}-oxiranyl)-benzoic acid methyl ester

: 4-(3-{(S)-1-[(4R,11S,14S)-4-(3-Chloro-4-methoxy-benzyl)-11-isobutyl-8,8-dimethyl-2,5,9,12-tetraoxo-10,13,17-trioxa-3,6-diaza-bicyclo[14.1.0]heptadec-14-yl]-ethyl}-oxiranyl)-benzoic acid methyl ester

Guidance literature:: With Oxone; sodium hydrogencarbonate; In dichloromethane; acetone; at 0 - 20 ℃; for 5h;
DOI:10.1021/jm0203884

Reference yield:

: 186256-66-6
cryptophycin-51

: 204398-12-9
4-(3-{(S)-1-[(E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-2,5,9,12-tetraoxo-1,4-dioxa-8,11-diaza-cyclohexadec-13-en-16-yl]-ethyl}-oxiranyl)-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: m-chloroperbenzoic acid / CH₂Cl₂ / 20 °C

2.1: 72 percent / aq. perchloric acid / 1,2-dimethoxy-ethane / 6 h / 20 °C

3.1: 98 percent / aq. NaIO₄ / tetrahydrofuran / 20 °C

4.1: sodium hydride / tetrahydrofuran / 1 h / 65 °C

4.2: 23 percent / tetrahydrofuran / 2 h / -78 - 20 °C

5.1: 33 percent / aq. NaHCO₃; oxone / acetone; CH₂Cl₂ / 5 h / 0 - 20 °C

With Oxone; sodium periodate; perchloric acid; sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; acetone; 4.2: Wittig reaction;
DOI:10.1021/jm0203884

Reference yield:

: 186256-68-8
cryptophycin 53

: 204398-12-9
4-(3-{(S)-1-[(E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-2,5,9,12-tetraoxo-1,4-dioxa-8,11-diaza-cyclohexadec-13-en-16-yl]-ethyl}-oxiranyl)-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 72 percent / aq. perchloric acid / 1,2-dimethoxy-ethane / 6 h / 20 °C

2.1: 98 percent / aq. NaIO₄ / tetrahydrofuran / 20 °C

3.1: sodium hydride / tetrahydrofuran / 1 h / 65 °C

3.2: 23 percent / tetrahydrofuran / 2 h / -78 - 20 °C

4.1: 33 percent / aq. NaHCO₃; oxone / acetone; CH₂Cl₂ / 5 h / 0 - 20 °C

With Oxone; sodium periodate; perchloric acid; sodium hydride; sodium hydrogencarbonate; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; acetone; 3.2: Wittig reaction;
DOI:10.1021/jm0203884