[4-((10S,14R,18S)-18-Carbamoylmethyl-14-naphthalen-1-ylmethyl-8,12,17,20-tetraoxo-7,11,16,19-tetraaza-spiro[5.14]icos-10-yl)-benzyl]-phosphonic acid dibenzyl ester

Base Information

• Chemical Name: [4-((10S,14R,18S)-18-Carbamoylmethyl-14-naphthalen-1-ylmethyl-8,12,17,20-tetraoxo-7,11,16,19-tetraaza-spiro[5.14]icos-10-yl)-benzyl]-phosphonic acid dibenzyl ester
• CAS No.: 562098-71-9
• Molecular Formula: C₅₀H₅₆N₅O₈P
• Molecular Weight: 885.997

Synonyms:[4-((10S,14R,18S)-18-Carbamoylmethyl-14-naphthalen-1-ylmethyl-8,12,17,20-tetraoxo-7,11,16,19-tetraaza-spiro[5.14]icos-10-yl)-benzyl]-phosphonic acid dibenzyl ester

Chemical Property of [4-((10S,14R,18S)-18-Carbamoylmethyl-14-naphthalen-1-ylmethyl-8,12,17,20-tetraoxo-7,11,16,19-tetraaza-spiro[5.14]icos-10-yl)-benzyl]-phosphonic acid dibenzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of [4-((10S,14R,18S)-18-Carbamoylmethyl-14-naphthalen-1-ylmethyl-8,12,17,20-tetraoxo-7,11,16,19-tetraaza-spiro[5.14]icos-10-yl)-benzyl]-phosphonic acid dibenzyl ester

There total 17 articles about [4-((10S,14R,18S)-18-Carbamoylmethyl-14-naphthalen-1-ylmethyl-8,12,17,20-tetraoxo-7,11,16,19-tetraaza-spiro[5.14]icos-10-yl)-benzyl]-phosphonic acid dibenzyl 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: 48.0%

(S)-2-[(1-{(S)-3-((R)-3-Aminomethyl-4-naphthalen-1-yl-butyrylamino)-3-[4-(bis-benzyloxy-phosphorylmethyl)-phenyl]-propionylamino}-cyclohexanecarbonyl)-amino]-succinamic acid; compound with trifluoro-acetic acid → [4-((10S,14R,18S)-18-Carbamoylmethyl-14-naphthalen-1-ylmethyl-8,12,17,20-tetraoxo-7,11,16,19-tetraaza-spiro[5.14]icos-10-yl)-benzyl]-phosphonic acid dibenzyl ester (562098-71-9)

Guidance literature:

With 4-methyl-morpholine; pentafluorophenyl diphenyl-phosphinate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jm030049q

Reference yield:

1-[((9H-fluoren-9-yl)methoxy)carbonylamino]cyclohexanecarboxylic acid (162648-54-6) → [4-((10S,14R,18S)-18-Carbamoylmethyl-14-naphthalen-1-ylmethyl-8,12,17,20-tetraoxo-7,11,16,19-tetraaza-spiro[5.14]icos-10-yl)-benzyl]-phosphonic acid dibenzyl ester (562098-71-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: HOBt; DIPCI / dimethylformamide / 0.17 h

1.2: 91 percent / iPr₂NEt / dimethylformamide

2.1: 92 percent / piperidine / dimethylformamide / 1 h / 20 °C

3.1: HOAt; EDC*HCl / dimethylformamide / 24 h / 20 °C

4.1: 246 mg / piperidine / dimethylformamide / 2 h

5.1: HOAt; EDC*HCl / dimethylformamide / 22 h / 20 °C

6.1: 100 percent / CH₂Cl₂ / 2 h / 20 °C

7.1: 48 percent / N-methylmorpholine; pentafluorophenyl diphenylphosphinate / dimethylformamide / 20 °C

With piperidine; 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; pentafluorophenyl diphenyl-phosphinate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diisopropyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm030049q

Reference yield:

(S)-2-(naphthalen-1-ylmethyl)pent-4-en-1-amine (350038-43-6) → [4-((10S,14R,18S)-18-Carbamoylmethyl-14-naphthalen-1-ylmethyl-8,12,17,20-tetraoxo-7,11,16,19-tetraaza-spiro[5.14]icos-10-yl)-benzyl]-phosphonic acid dibenzyl ester (562098-71-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 94 percent / Et₃N / methanol / 20 °C

2: N-methylmorpholine N-oxide; aq. OsO₄ / tetrahydrofuran / 20 °C

3: aq. NaIO₄ / tetrahydrofuran / 3.5 h

4: 76 percent / pyridinium chlorochromate; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

5: 86 percent / aq. LiOH / tetrahydrofuran / 2 h / 20 °C

6: HOAt; EDC*HCl / dimethylformamide / 22 h / 20 °C

7: 100 percent / CH₂Cl₂ / 2 h / 20 °C

8: 48 percent / N-methylmorpholine; pentafluorophenyl diphenylphosphinate / dimethylformamide / 20 °C

With 4-methyl-morpholine; lithium hydroxide; sodium periodate; osmium(VIII) oxide; 1-hydroxy-7-aza-benzotriazole; 4 A molecular sieve; pentafluorophenyl diphenyl-phosphinate; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm030049q

upstream raw materials:

1-[((9H-fluoren-9-yl)methoxy)carbonylamino]cyclohexanecarboxylic acid

(S)-2-(naphthalen-1-ylmethyl)pent-4-en-1-amine

(S)-3-[4-(Bis-benzyloxy-phosphorylmethyl)-phenyl]-3-((R)-2-methyl-propane-2-sulfinylamino)-propionic acid methyl ester

(2S)-2-(naphthalen-1-ylmethylpent-4-enyl)carbamic acid tert-butyl ester

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