(S)-2-[(3S,6S,11R,18R)-11-tert-Butoxycarbonylamino-3-butyl-6-(4-hydroxy-benzyl)-2,5,8,12,19-pentaoxo-1,4,7,13-tetraaza-cyclononadec-18-ylamino]-3-(1H-indol-3-yl)-propionic acid

Base Information

Chemical Name:(S)-2-[(3S,6S,11R,18R)-11-tert-Butoxycarbonylamino-3-butyl-6-(4-hydroxy-benzyl)-2,5,8,12,19-pentaoxo-1,4,7,13-tetraaza-cyclononadec-18-ylamino]-3-(1H-indol-3-yl)-propionic acid
CAS No.:120059-55-4
Molecular Formula:C₄₂H₅₇N₇O₁₀
Molecular Weight:819.955
Hs Code.:

(S)-2-[(3S,6S,11R,18R)-11-tert-Butoxycarbonylamino-3-butyl-6-(4-hydroxy-benzyl)-2,5,8,12,19-pentaoxo-1,4,7,13-tetraaza-cyclononadec-18-ylamino]-3-(1H-indol-3-yl)-propionic acid

Synonyms:(S)-2-[(3S,6S,11R,18R)-11-tert-Butoxycarbonylamino-3-butyl-6-(4-hydroxy-benzyl)-2,5,8,12,19-pentaoxo-1,4,7,13-tetraaza-cyclononadec-18-ylamino]-3-(1H-indol-3-yl)-propionic acid

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Chemical Property of (S)-2-[(3S,6S,11R,18R)-11-tert-Butoxycarbonylamino-3-butyl-6-(4-hydroxy-benzyl)-2,5,8,12,19-pentaoxo-1,4,7,13-tetraaza-cyclononadec-18-ylamino]-3-(1H-indol-3-yl)-propionic acid

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Technology Process of (S)-2-[(3S,6S,11R,18R)-11-tert-Butoxycarbonylamino-3-butyl-6-(4-hydroxy-benzyl)-2,5,8,12,19-pentaoxo-1,4,7,13-tetraaza-cyclononadec-18-ylamino]-3-(1H-indol-3-yl)-propionic acid

There total 5 articles about (S)-2-[(3S,6S,11R,18R)-11-tert-Butoxycarbonylamino-3-butyl-6-(4-hydroxy-benzyl)-2,5,8,12,19-pentaoxo-1,4,7,13-tetraaza-cyclononadec-18-ylamino]-3-(1H-indol-3-yl)-propionic acid 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: 81.0%

: 115295-05-1
(S)-2-[(3S,6S,11R,18R)-11-tert-Butoxycarbonylamino-3-butyl-6-(4-hydroxy-benzyl)-2,5,8,12,19-pentaoxo-1,4,7,13-tetraaza-cyclononadec-18-ylamino]-3-(1H-indol-3-yl)-propionic acid methyl ester

: 120059-55-4
(S)-2-[(3S,6S,11R,18R)-11-tert-Butoxycarbonylamino-3-butyl-6-(4-hydroxy-benzyl)-2,5,8,12,19-pentaoxo-1,4,7,13-tetraaza-cyclononadec-18-ylamino]-3-(1H-indol-3-yl)-propionic acid

Guidance literature:: With sodium hydroxide; In methanol; 1.) 0 deg C, 2 h, 2.) r.t., 24 h;
DOI:10.1021/jm00126a007

Reference yield:

: 34404-30-3
N-(tert-butoxycarbonyl)-D-glutamic acid 1-benzyl ester

: 120059-55-4
(S)-2-[(3S,6S,11R,18R)-11-tert-Butoxycarbonylamino-3-butyl-6-(4-hydroxy-benzyl)-2,5,8,12,19-pentaoxo-1,4,7,13-tetraaza-cyclononadec-18-ylamino]-3-(1H-indol-3-yl)-propionic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 81 percent / Et₃N, N-hydroxysuccinimide, N,N'-dicyclohexylcarbodiimide / dimethylformamide / 1.) chilling, 1 h, 2.) r.t., overnight

2: 95 percent / H₂ / 10 percent Pd/C / methanol / 3 h

3: 40 percent / Et₃N, diphenyl phosphorazidate / dimethylformamide / pH 7 to 7.5; 1.) -25 deg C, 48 h, 2.) 4 deg C, 48 h

4: 81 percent / 1 N NaOH / methanol / 1.) 0 deg C, 2 h, 2.) r.t., 24 h

With sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; diphenyl phosphoryl azide; hydrogen; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;
DOI:10.1021/jm00126a007

Reference yield:

: 107326-81-8
H-Tyr-Nle-D-Lys(Z)-Trp-OCH₃

: 120059-55-4
(S)-2-[(3S,6S,11R,18R)-11-tert-Butoxycarbonylamino-3-butyl-6-(4-hydroxy-benzyl)-2,5,8,12,19-pentaoxo-1,4,7,13-tetraaza-cyclononadec-18-ylamino]-3-(1H-indol-3-yl)-propionic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 81 percent / Et₃N, N-hydroxysuccinimide, N,N'-dicyclohexylcarbodiimide / dimethylformamide / 1.) chilling, 1 h, 2.) r.t., overnight

2: 95 percent / H₂ / 10 percent Pd/C / methanol / 3 h

3: 40 percent / Et₃N, diphenyl phosphorazidate / dimethylformamide / pH 7 to 7.5; 1.) -25 deg C, 48 h, 2.) 4 deg C, 48 h

4: 81 percent / 1 N NaOH / methanol / 1.) 0 deg C, 2 h, 2.) r.t., 24 h

With sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; diphenyl phosphoryl azide; hydrogen; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;
DOI:10.1021/jm00126a007