2-{1-[2-carbamoyl-1-(3-naphthalen-1-yl-propylcarbamoyl)-ethylcarbamoyl]-cyclohexylcarbamoyl}-3-[4-(di-tert-butoxy-phosphorylmethyl)-phenyl]-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

Base Information

• Chemical Name: 2-{1-[2-carbamoyl-1-(3-naphthalen-1-yl-propylcarbamoyl)-ethylcarbamoyl]-cyclohexylcarbamoyl}-3-[4-(di-tert-butoxy-phosphorylmethyl)-phenyl]-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester
• CAS No.: 525575-18-2
• Molecular Formula: C₆₀H₇₄N₅O₉P
• Molecular Weight: 1040.25
• Mol file: 525575-18-2.mol

Synonyms:2-{1-[2-carbamoyl-1-(3-naphthalen-1-yl-propylcarbamoyl)-ethylcarbamoyl]-cyclohexylcarbamoyl}-3-[4-(di-tert-butoxy-phosphorylmethyl)-phenyl]-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

Chemical Property of 2-{1-[2-carbamoyl-1-(3-naphthalen-1-yl-propylcarbamoyl)-ethylcarbamoyl]-cyclohexylcarbamoyl}-3-[4-(di-tert-butoxy-phosphorylmethyl)-phenyl]-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{1-[2-carbamoyl-1-(3-naphthalen-1-yl-propylcarbamoyl)-ethylcarbamoyl]-cyclohexylcarbamoyl}-3-[4-(di-tert-butoxy-phosphorylmethyl)-phenyl]-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

There total 11 articles about 2-{1-[2-carbamoyl-1-(3-naphthalen-1-yl-propylcarbamoyl)-ethylcarbamoyl]-cyclohexylcarbamoyl}-3-[4-(di-tert-butoxy-phosphorylmethyl)-phenyl]-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl 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: 100.0%

(2S)-2-amino-N1-[3-(1-naphthalenyl)propyl]butanediamide (220193-52-2) + (2S,3R)-1-((fluoren-9-ylmethyl)oxycarbonyl)-3-(4-((bis-(tert-butyl)phosphono)methyl)phenyl)piperidine-2-carboxylic acid (510773-78-1) → 2-{1-[2-carbamoyl-1-(3-naphthalen-1-yl-propylcarbamoyl)-ethylcarbamoyl]-cyclohexylcarbamoyl}-3-[4-(di-tert-butoxy-phosphorylmethyl)-phenyl]-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (525575-18-2)

Guidance literature:

With benzotriazol-1-ol; diisopropyl-carbodiimide; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/S0040-4020(02)01421-7

Reference yield:

3-(3-(4-((bis(tert-butyl)phosphono)methyl)phenyl)prop-2-enoyl)-4(S)-benzyl-1,3-oxazolidin-2-one → 2-{1-[2-carbamoyl-1-(3-naphthalen-1-yl-propylcarbamoyl)-ethylcarbamoyl]-cyclohexylcarbamoyl}-3-[4-(di-tert-butoxy-phosphorylmethyl)-phenyl]-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (525575-18-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 80 percent / CuBr*SMe₂ / tetrahydrofuran / 2.5 h / -78 °C

2.1: BH₃ / tetrahydrofuran / 1 h / 0 °C

2.2: 90 percent / NaBO₃*H₂O / tetrahydrofuran; H₂O / 3 h / 20 °C

3.1: 82 percent / imidazole / dimethylformamide / 20 °C

4.1: KHMDS / tetrahydrofuran; toluene / 0.67 h / -78 °C

4.2: 35 percent / trisyl azide / tetrahydrofuran / 0.03 h / -78 °C

5.1: 87 percent / HF*pyridine / tetrahydrofuran / 0 - 20 °C

6.1: oxalyl chloride; Et₃N; DMSO / CH₂Cl₂ / -78 - 20 °C

7.1: 17 mg / H₂ / 10 percent Pd-C / 20 °C / 2068.59 Torr

8.1: NaOH / dioxane; H₂O / 2 h / 0 °C

9.1: 12 mg / dry ice / dioxane; H₂O / 20 °C

10.1: 100 percent / HOBt; 1,3-diisopropylcarbodiimide / dimethylformamide / 20 °C

With 1H-imidazole; sodium hydroxide; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; Methamphetamin; borane; hydrogen; potassium hexamethylsilazane; benzotriazol-1-ol; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; diisopropyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: Michael addition / 6.1: Swern oxidation;

DOI:10.1016/S0040-4020(02)01421-7

Reference yield:

(4S)-3-((3S)-3-(4-((bis-(tert-butyl)phosphono)methyl)phenyl)hex-5-enoyl)-4-benzyl-1,3-oxazolidin-2-one (510773-80-5) → 2-{1-[2-carbamoyl-1-(3-naphthalen-1-yl-propylcarbamoyl)-ethylcarbamoyl]-cyclohexylcarbamoyl}-3-[4-(di-tert-butoxy-phosphorylmethyl)-phenyl]-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (525575-18-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: BH₃ / tetrahydrofuran / 1 h / 0 °C

1.2: 90 percent / NaBO₃*H₂O / tetrahydrofuran; H₂O / 3 h / 20 °C

2.1: 82 percent / imidazole / dimethylformamide / 20 °C

3.1: KHMDS / tetrahydrofuran; toluene / 0.67 h / -78 °C

3.2: 35 percent / trisyl azide / tetrahydrofuran / 0.03 h / -78 °C

4.1: 87 percent / HF*pyridine / tetrahydrofuran / 0 - 20 °C

5.1: oxalyl chloride; Et₃N; DMSO / CH₂Cl₂ / -78 - 20 °C

6.1: 17 mg / H₂ / 10 percent Pd-C / 20 °C / 2068.59 Torr

7.1: NaOH / dioxane; H₂O / 2 h / 0 °C

8.1: 12 mg / dry ice / dioxane; H₂O / 20 °C

9.1: 100 percent / HOBt; 1,3-diisopropylcarbodiimide / dimethylformamide / 20 °C

With 1H-imidazole; sodium hydroxide; oxalyl dichloride; Methamphetamin; borane; hydrogen; potassium hexamethylsilazane; benzotriazol-1-ol; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; diisopropyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 5.1: Swern oxidation;

DOI:10.1016/S0040-4020(02)01421-7

upstream raw materials:

(2S)-2-amino-N₁-[3-(1-naphthalenyl)propyl]butanediamide

(2S,3R)-1-((fluoren-9-ylmethyl)oxycarbonyl)-3-(4-((bis-(tert-butyl)phosphono)methyl)phenyl)piperidine-2-carboxylic acid

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

methyl (2S,3R)-3-(4-((bis-(tert-butyl)phosphono)methyl)phenyl)piperidine-2-carboxylate

Downstream raw materials:

{2-{1-[2-carbamoyl-1-(3-naphthalen-1-yl-propylcarbamoyl)-ethylcarbamoyl]-cyclohexylcarbamoyl}-3-[4-(di-tert-butoxy-phosphorylmethyl)-phenyl]-piperidin-1-yl}-oxo-acetic acid tert-butyl ester