(3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)-4,5-dimethoxyphenyl]-4-(tert-butyldimethylsilyloxymethyl)-3-methylpyrrolidine-2,2-dicarboxylate

Base Information

• Chemical Name: (3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)-4,5-dimethoxyphenyl]-4-(tert-butyldimethylsilyloxymethyl)-3-methylpyrrolidine-2,2-dicarboxylate
• CAS No.: 1455451-97-4
• Molecular Formula: C₃₅H₅₃NO₈Si
• Molecular Weight: 643.893
• Mol file: 1455451-97-4.mol

Synonyms:(3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)-4,5-dimethoxyphenyl]-4-(tert-butyldimethylsilyloxymethyl)-3-methylpyrrolidine-2,2-dicarboxylate

Chemical Property of (3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)-4,5-dimethoxyphenyl]-4-(tert-butyldimethylsilyloxymethyl)-3-methylpyrrolidine-2,2-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)-4,5-dimethoxyphenyl]-4-(tert-butyldimethylsilyloxymethyl)-3-methylpyrrolidine-2,2-dicarboxylate

There total 7 articles about (3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)-4,5-dimethoxyphenyl]-4-(tert-butyldimethylsilyloxymethyl)-3-methylpyrrolidine-2,2-dicarboxylate 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: 72.0%

(3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)-4,5-dimethoxyphenyl]-4-hydroxymethyl-3-methylpyrrolidine-2,2-dicarboxylate (1455451-94-1) + tert-butyldimethylsilyl chloride (18162-48-6) → (3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)-4,5-dimethoxyphenyl]-4-(tert-butyldimethylsilyloxymethyl)-3-methylpyrrolidine-2,2-dicarboxylate (1455451-97-4)

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 20 ℃; for 8h; Inert atmosphere;

DOI:10.1016/j.tet.2013.08.012

Reference yield:

(E)-diethyl N-[2-(2-benzyloxyethyl)-4,5-dimethoxybenzylideneamino]malonate (1455451-88-3) → (3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)-4,5-dimethoxyphenyl]-4-(tert-butyldimethylsilyloxymethyl)-3-methylpyrrolidine-2,2-dicarboxylate (1455451-97-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: (S)-diphenylprolinol / tetrahydrofuran / 0.5 h / 4 °C / Inert atmosphere

1.2: 72 h / 4 °C

2.1: sodium tetrahydroborate; methanol / 0 °C / Inert atmosphere

3.1: dmap; 1H-imidazole / N,N-dimethyl-formamide / 8 h / 20 °C / Inert atmosphere

With 1H-imidazole; methanol; dmap; sodium tetrahydroborate; (S)-diphenylprolinol; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2013.08.012

Reference yield:

(3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)-4,5-dimethoxyphenyl]-4-formyl-3-methylpyrrolidine-2,2-dicarboxylate (1455451-91-8) → (3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)-4,5-dimethoxyphenyl]-4-(tert-butyldimethylsilyloxymethyl)-3-methylpyrrolidine-2,2-dicarboxylate (1455451-97-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate; methanol / 0 °C / Inert atmosphere

2: dmap; 1H-imidazole / N,N-dimethyl-formamide / 8 h / 20 °C / Inert atmosphere

With 1H-imidazole; methanol; dmap; sodium tetrahydroborate; In N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2013.08.012

upstream raw materials:

(E)-diethyl N-[2-(2-benzyloxyethyl)-4,5-dimethoxybenzylideneamino]malonate

(3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)-4,5-dimethoxyphenyl]-4-formyl-3-methylpyrrolidine-2,2-dicarboxylate

(3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)-4,5-dimethoxyphenyl]-4-hydroxymethyl-3-methylpyrrolidine-2,2-dicarboxylate

tert-butyldimethylsilyl chloride

Downstream raw materials:

(3R,4R,5S)-diethyl 4-(tert-butyldimethylsilyloxymethyl)-5-[2-(2-hydroxyethyl)-4,5-dimethoxyphenyl]-3-methylpyrrolidine-2,2-dicarboxylate