(2R,3R,4R,5R)-2-[(1S)-tert-butoxycarbonyl-2-phenylethylcarbamoyl]-5-(dimethoxyphosphoryl)-4-[2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)ethyl]-3-isobutylpyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2R,3R,4R,5R)-2-[(1S)-tert-butoxycarbonyl-2-phenylethylcarbamoyl]-5-(dimethoxyphosphoryl)-4-[2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)ethyl]-3-isobutylpyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 885503-51-5
• Molecular Formula: C₄₃H₅₆N₃O₁₀P
• Molecular Weight: 805.905
• Mol file: 885503-51-5.mol

Synonyms:(2R,3R,4R,5R)-2-[(1S)-tert-butoxycarbonyl-2-phenylethylcarbamoyl]-5-(dimethoxyphosphoryl)-4-[2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)ethyl]-3-isobutylpyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of (2R,3R,4R,5R)-2-[(1S)-tert-butoxycarbonyl-2-phenylethylcarbamoyl]-5-(dimethoxyphosphoryl)-4-[2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)ethyl]-3-isobutylpyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R)-2-[(1S)-tert-butoxycarbonyl-2-phenylethylcarbamoyl]-5-(dimethoxyphosphoryl)-4-[2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)ethyl]-3-isobutylpyrrolidine-1-carboxylic acid tert-butyl ester

There total 12 articles about (2R,3R,4R,5R)-2-[(1S)-tert-butoxycarbonyl-2-phenylethylcarbamoyl]-5-(dimethoxyphosphoryl)-4-[2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)ethyl]-3-isobutylpyrrolidine-1-carboxylic acid tert-butyl 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:

5-(dimethoxy-phosphoryl)-4-[2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-ethyl]-3-isobutyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester + L-phenylalanine tert-butyl ester hydrochloride (15100-75-1,75898-47-4) → (2R,3R,4R,5R)-2-[(1S)-tert-butoxycarbonyl-2-phenylethylcarbamoyl]-5-(dimethoxyphosphoryl)-4-[2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)ethyl]-3-isobutylpyrrolidine-1-carboxylic acid tert-butyl ester (885503-51-5)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

DOI:10.1021/jo052649y

Reference yield:

(3R,4R,5R)-3-Allyl-5-hydroxymethyl-4-isobutyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester → (2R,3R,4R,5R)-2-[(1S)-tert-butoxycarbonyl-2-phenylethylcarbamoyl]-5-(dimethoxyphosphoryl)-4-[2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)ethyl]-3-isobutylpyrrolidine-1-carboxylic acid tert-butyl ester (885503-51-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: Jones' reagent / acetone / 20 °C

2.1: 0.8 g / diethyl ether / 1 h / 0 °C

3.1: LiEt₃BH / tetrahydrofuran / -78 °C

3.2: Ac₂O; Et₃N; DMAP / CH₂Cl₂ / 20 °C

3.3: 58 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 - 20 °C

4.1: ozone / CH₂Cl₂; methanol / -78 °C

4.2: Me₂S / CH₂Cl₂; methanol / -78 - 0 °C

5.1: NaBH₄ / methanol / 0 - 20 °C

6.1: Et₃N; DMAP / CH₂Cl₂ / 20 °C

7.1: 100 mg / NaH / dimethylformamide; various solvent(s) / 20 °C

8.1: LiOH*H₂O / tetrahydrofuran; H₂O; methanol / 20 °C

9.1: 63 mg / ethyldiisopropylamine; HOBt; EDCI / CH₂Cl₂ / 20 °C

With dmap; lithium hydroxide; sodium tetrahydroborate; jones' reagent; sodium hydride; lithium triethylborohydride; benzotriazol-1-ol; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo052649y

Reference yield:

(2R,3R,4R)-4-allyl-3-isobutyl-5-oxopyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (885503-48-0) → (2R,3R,4R,5R)-2-[(1S)-tert-butoxycarbonyl-2-phenylethylcarbamoyl]-5-(dimethoxyphosphoryl)-4-[2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)ethyl]-3-isobutylpyrrolidine-1-carboxylic acid tert-butyl ester (885503-51-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: LiEt₃BH / tetrahydrofuran / -78 °C

1.2: Ac₂O; Et₃N; DMAP / CH₂Cl₂ / 20 °C

1.3: 58 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 - 20 °C

2.1: ozone / CH₂Cl₂; methanol / -78 °C

2.2: Me₂S / CH₂Cl₂; methanol / -78 - 0 °C

3.1: NaBH₄ / methanol / 0 - 20 °C

4.1: Et₃N; DMAP / CH₂Cl₂ / 20 °C

5.1: 100 mg / NaH / dimethylformamide; various solvent(s) / 20 °C

6.1: LiOH*H₂O / tetrahydrofuran; H₂O; methanol / 20 °C

7.1: 63 mg / ethyldiisopropylamine; HOBt; EDCI / CH₂Cl₂ / 20 °C

With dmap; lithium hydroxide; sodium tetrahydroborate; sodium hydride; lithium triethylborohydride; benzotriazol-1-ol; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo052649y

upstream raw materials:

L-phenylalanine tert-butyl ester hydrochloride

(2R,3R,4R)-4-allyl-3-isobutyl-5-oxopyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

(2R,3R,4R,5R)-4-allyl-5-(dimethoxyphosphoryl)-3-isobutylpyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

(2R,3R)-2-(tert-butyldiphenylsilanyloxymethyl)-3-isobutyl-5-oxopyrrolidine-1-carboxylic acid tert-butyl ester