(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

Base Information

• Chemical Name: (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
• CAS No.: 366793-06-8
• Molecular Formula: C₃₉H₄₈Cl₃N₇O₁₂
• Molecular Weight: 913.209
• Mol file: 366793-06-8.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 17 articles about (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 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: 54.0%

3-[benzyloxy-({[(carboxymethyl-carbamoyl)-methyl]-methyl-carbamoyl}-methyl)-carbamoyl]-2-[4-methyl-3-methylaminoacetoxy-2-(2,2,2-trichloro-ethoxycarbonylamino)-pentanoyl]-tetrahydro-pyridazine-1-carboxylic acid benzyl ester → (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 (366793-06-8)

Guidance literature:

With N-ethylmorpholine;; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; In dichloromethane; at 0 - 20 ℃; for 48h; Inert atmosphere;

DOI:10.1039/c9cc06169j

Reference yield:

(R)-3-[Benzyloxy-({[(carboxymethyl-carbamoyl)-methyl]-methyl-carbamoyl}-methyl)-carbamoyl]-2-[(2S,3S)-4-methyl-3-(2-methylamino-acetoxy)-2-(2,2,2-trichloro-ethoxycarbonylamino)-pentanoyl]-tetrahydro-pyridazine-1-carboxylic acid benzyl ester; compound with trifluoro-acetic acid → (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 (366793-06-8)

Guidance literature:

With N-Ethylmaleimide; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ol016440s

Reference yield:

N'-{[2-(benzyloxycarbonyl-methyl-amino)-acetylamino]-acetyl}-hydrazinecarboxylic acid tert-butyl ester (366792-99-6) → (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 (366793-06-8)

Guidance literature:

Multi-step reaction with 6 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

With N-Ethylmaleimide; silver cyanide; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; 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

upstream raw materials:

D-(N^α-Fmoc,N^δ-Cbz)-Piz-Cl

(3R)-N⁽¹⁾-Z-N⁽²⁾-Fmoc-piperazic acid

(2S,3S)-N-Troc-3-hydroxyleucine allyl ester

N'-[(2-methylamino-acetylamino)-acetyl]-hydrazinecarboxylic acid tert-butyl ester

Downstream raw materials:

(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