(4aR,19S,20S)-6-Benzyloxy-20-benzyloxycarbonylamino-19-isopropyl-9,15-dimethyl-5,8,11,14,17,21-hexaoxo-octadecahydro-18-oxa-1,6,9,12,15,21a-hexaaza-benzocyclononadecene-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(4aR,19S,20S)-6-Benzyloxy-20-benzyloxycarbonylamino-19-isopropyl-9,15-dimethyl-5,8,11,14,17,21-hexaoxo-octadecahydro-18-oxa-1,6,9,12,15,21a-hexaaza-benzocyclononadecene-1-carboxylic acid benzyl ester
CAS No.:366793-07-9
Molecular Formula:C₄₄H₅₃N₇O₁₂
Molecular Weight:871.945
Hs Code.:

(4aR,19S,20S)-6-Benzyloxy-20-benzyloxycarbonylamino-19-isopropyl-9,15-dimethyl-5,8,11,14,17,21-hexaoxo-octadecahydro-18-oxa-1,6,9,12,15,21a-hexaaza-benzocyclononadecene-1-carboxylic acid benzyl ester

Synonyms:(4aR,19S,20S)-6-Benzyloxy-20-benzyloxycarbonylamino-19-isopropyl-9,15-dimethyl-5,8,11,14,17,21-hexaoxo-octadecahydro-18-oxa-1,6,9,12,15,21a-hexaaza-benzocyclononadecene-1-carboxylic acid benzyl ester

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Chemical Property of (4aR,19S,20S)-6-Benzyloxy-20-benzyloxycarbonylamino-19-isopropyl-9,15-dimethyl-5,8,11,14,17,21-hexaoxo-octadecahydro-18-oxa-1,6,9,12,15,21a-hexaaza-benzocyclononadecene-1-carboxylic acid benzyl ester

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Technology Process of (4aR,19S,20S)-6-Benzyloxy-20-benzyloxycarbonylamino-19-isopropyl-9,15-dimethyl-5,8,11,14,17,21-hexaoxo-octadecahydro-18-oxa-1,6,9,12,15,21a-hexaaza-benzocyclononadecene-1-carboxylic acid benzyl ester

There total 18 articles about (4aR,19S,20S)-6-Benzyloxy-20-benzyloxycarbonylamino-19-isopropyl-9,15-dimethyl-5,8,11,14,17,21-hexaoxo-octadecahydro-18-oxa-1,6,9,12,15,21a-hexaaza-benzocyclononadecene-1-carboxylic acid benzyl 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: 79.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: 366793-06-8
(4aR,19S,20S)-6-Benzyloxy-19-isopropyl-9,15-dimethyl-5,8,11,14,17,21-hexaoxo-20-(2,2,2-trichloro-ethoxycarbonylamino)-octadecahydro-18-oxa-1,6,9,12,15,21a-hexaaza-benzocyclononadecene-1-carboxylic acid benzyl ester

: 366793-07-9
(4aR,19S,20S)-6-Benzyloxy-20-benzyloxycarbonylamino-19-isopropyl-9,15-dimethyl-5,8,11,14,17,21-hexaoxo-octadecahydro-18-oxa-1,6,9,12,15,21a-hexaaza-benzocyclononadecene-1-carboxylic acid benzyl ester

Guidance literature:: (4aR,19S,20S)-6-Benzyloxy-19-isopropyl-9,15-dimethyl-5,8,11,14,17,21-hexaoxo-20-(2,2,2-trichloro-ethoxycarbonylamino)-octadecahydro-18-oxa-1,6,9,12,15,21a-hexaaza-benzocyclononadecene-1-carboxylic acid benzyl ester; With acetic acid; zinc; In water; at 20 ℃; for 2h;

benzyl chloroformate; With sodium hydrogencarbonate; In water; at 0 - 20 ℃; for 2h;
DOI:10.1039/c9cc06169j

Reference yield:

: 366792-99-6
N'-{[2-(benzyloxycarbonyl-methyl-amino)-acetylamino]-acetyl}-hydrazinecarboxylic acid tert-butyl ester

: 366793-07-9
(4aR,19S,20S)-6-Benzyloxy-20-benzyloxycarbonylamino-19-isopropyl-9,15-dimethyl-5,8,11,14,17,21-hexaoxo-octadecahydro-18-oxa-1,6,9,12,15,21a-hexaaza-benzocyclononadecene-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 100 percent / H₂ / 20percent Pd(OH)2/C / methanol / 8 h / 20 °C

2.1: BOP-Cl; Et₃N / CH₂Cl₂ / -20 - 0 °C

3.1: 87 percent / Et₂NH / acetonitrile / 0.33 h / 20 °C

4.1: AgCN / benzene / 0.05 h / 75 - 80 °C

5.1: CH₂Cl₂ / 2 h / 20 °C

5.2: NBS; H₂O / tetrahydrofuran / 2 h / 20 °C

6.1: NEM; HATU / CH₂Cl₂ / 0 - 20 °C

7.1: aq. NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

With N-Ethylmaleimide; silver cyanide; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium hydrogencarbonate; diethylamine; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 20percent Pd(OH)2/C; In methanol; dichloromethane; acetonitrile; benzene;
DOI:10.1021/ol016440s

Reference yield:

: 366792-94-1
(tert-Butoxycarbonyl-methyl-amino)-acetic acid (S)-1-[(S)-chlorocarbonyl-(2,2,2-trichloro-ethoxycarbonylamino)-methyl]-2-methyl-propyl ester

: 366793-07-9
(4aR,19S,20S)-6-Benzyloxy-20-benzyloxycarbonylamino-19-isopropyl-9,15-dimethyl-5,8,11,14,17,21-hexaoxo-octadecahydro-18-oxa-1,6,9,12,15,21a-hexaaza-benzocyclononadecene-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: AgCN / benzene / 0.05 h / 75 - 80 °C

2.1: CH₂Cl₂ / 2 h / 20 °C

2.2: NBS; H₂O / tetrahydrofuran / 2 h / 20 °C

3.1: NEM; HATU / CH₂Cl₂ / 0 - 20 °C

4.1: aq. NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

With N-Ethylmaleimide; silver cyanide; sodium hydrogencarbonate; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; benzene;
DOI:10.1021/ol016440s