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

Base Information

• Chemical Name: (3R,4R,5R)-3-allyl-5-(tert-butyldiphenylsilanyloxymethyl)-4-isobutyl-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 885503-47-9
• Molecular Formula: C₃₃H₄₇NO₄Si
• Molecular Weight: 549.826
• Mol file: 885503-47-9.mol

Synonyms:(3R,4R,5R)-3-allyl-5-(tert-butyldiphenylsilanyloxymethyl)-4-isobutyl-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of (3R,4R,5R)-3-allyl-5-(tert-butyldiphenylsilanyloxymethyl)-4-isobutyl-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5R)-3-allyl-5-(tert-butyldiphenylsilanyloxymethyl)-4-isobutyl-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester

There total 2 articles about (3R,4R,5R)-3-allyl-5-(tert-butyldiphenylsilanyloxymethyl)-4-isobutyl-2-oxopyrrolidine-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: 37.0%

(2R,3R)-2-(tert-butyldiphenylsilanyloxymethyl)-3-isobutyl-5-oxopyrrolidine-1-carboxylic acid tert-butyl ester (885503-46-8) + allyl iodid (556-56-9) → (3S,4R,5R)-3-allyl-5-(tert-butyldiphenylsilanyloxymethyl)-4-isobutyl-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester + (3R,4R,5R)-3-allyl-5-(tert-butyldiphenylsilanyloxymethyl)-4-isobutyl-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester (885503-47-9)

Guidance literature:

(2R,3R)-2-(tert-butyldiphenylsilanyloxymethyl)-3-isobutyl-5-oxopyrrolidine-1-carboxylic acid tert-butyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

allyl iodid; In tetrahydrofuran; at -78 ℃;

DOI:10.1021/jo052649y

Reference yield:

2-(tert-butyl-diphenylsilanyloxymethyl)-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester → (3R,4R,5R)-3-allyl-5-(tert-butyldiphenylsilanyloxymethyl)-4-isobutyl-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester (885503-47-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: CuI / diethyl ether / 0.25 h / -20 °C

1.2: 87 percent / diethyl ether / 3 h / -20 °C

2.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: 37 percent / tetrahydrofuran / -78 °C

With copper(l) iodide; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jo052649y

Reference yield:

(3R,4R,5R)-3-allyl-5-(tert-butyldiphenylsilanyloxymethyl)-4-isobutyl-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester (885503-47-9) → (2R,3R,4R,5R)-5-(dimethoxyphosphoryl)-4-[2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)ethyl]-2-[(1S)-methoxycarbonyl-3-phenylpropylcarbamoyl]-3-isobutylpyrrolidine-1-carboxylic acid tert-butyl ester (885503-52-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: glacial acetic acid; TBAF / tetrahydrofuran / 48 h / 20 °C

2.1: Jones' reagent / acetone / 20 °C

3.1: 0.8 g / diethyl ether / 1 h / 0 °C

4.1: LiEt₃BH / tetrahydrofuran / -78 °C

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

4.3: 58 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 - 20 °C

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

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

6.1: NaBH₄ / methanol / 0 - 20 °C

7.1: Et₃N; DMAP / CH₂Cl₂ / 20 °C

8.1: 100 mg / NaH / dimethylformamide; various solvent(s) / 20 °C

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

10.1: 49 mg / ethyldiisopropylamine; HOBt; EDCI / CH₂Cl₂ / 20 °C

With dmap; lithium hydroxide; sodium tetrahydroborate; jones' reagent; tetrabutyl ammonium fluoride; sodium hydride; lithium triethylborohydride; benzotriazol-1-ol; ozone; acetic acid; 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

upstream raw materials:

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

allyl iodid

Downstream raw materials:

(2R,3R,4R,5R)-5-(dimethoxyphosphoryl)-4-[2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)ethyl]-2-[(1S)-methoxycarbonyl-3-phenylpropylcarbamoyl]-3-isobutylpyrrolidine-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