(2S,3S,4R)-1-benzyl-3,4-bis(benzyloxy)-2-(4-(tert-butyldimethylsilyloxy)butyl)pyrrolidine

Base Information

• Chemical Name: (2S,3S,4R)-1-benzyl-3,4-bis(benzyloxy)-2-(4-(tert-butyldimethylsilyloxy)butyl)pyrrolidine
• CAS No.: 1357981-31-7
• Molecular Formula: C₃₅H₄₉NO₃Si
• Molecular Weight: 559.864
• Mol file: 1357981-31-7.mol

Synonyms:(2S,3S,4R)-1-benzyl-3,4-bis(benzyloxy)-2-(4-(tert-butyldimethylsilyloxy)butyl)pyrrolidine

Chemical Property of (2S,3S,4R)-1-benzyl-3,4-bis(benzyloxy)-2-(4-(tert-butyldimethylsilyloxy)butyl)pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R)-1-benzyl-3,4-bis(benzyloxy)-2-(4-(tert-butyldimethylsilyloxy)butyl)pyrrolidine

There total 5 articles about (2S,3S,4R)-1-benzyl-3,4-bis(benzyloxy)-2-(4-(tert-butyldimethylsilyloxy)butyl)pyrrolidine 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: 95.0%

(2R,3S,4S)-4-(benzylamino)-2,3-bis(benzyloxy)-8-(tert-butyldimethylsilyloxy)octan-1-ol (1357981-14-6) → (2S,3S,4R)-1-benzyl-3,4-bis(benzyloxy)-2-(4-(tert-butyldimethylsilyloxy)butyl)pyrrolidine (1357981-31-7)

Guidance literature:

With carbon tetrabromide; triethylamine; triphenylphosphine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/j.tet.2011.12.063

Reference yield:

(2R,3R,4R)-3,4-bis(benzyloxy)-tetrahydrofuran-2-ol (1357981-23-7) → (2S,3S,4R)-1-benzyl-3,4-bis(benzyloxy)-2-(4-(tert-butyldimethylsilyloxy)butyl)pyrrolidine (1357981-31-7)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene / 10 h / 50 °C / Molecular sieve; Inert atmosphere

2: tetrahydrofuran / -78 - 20 °C / Inert atmosphere

3: carbon tetrabromide; triethylamine; triphenylphosphine / dichloromethane / 2 h / 0 °C

With carbon tetrabromide; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/j.tet.2011.12.063

Reference yield:

(2R,3R)-2,3-bis(benzyloxy)-4-hydroxybutanoic acid 1,4-lactone (130412-79-2) → (2S,3S,4R)-1-benzyl-3,4-bis(benzyloxy)-2-(4-(tert-butyldimethylsilyloxy)butyl)pyrrolidine (1357981-31-7)

Guidance literature:

Multi-step reaction with 4 steps

1: diisobutylaluminium hydride / tetrahydrofuran; dichloromethane / 2 h / -78 °C

2: toluene / 10 h / 50 °C / Molecular sieve; Inert atmosphere

3: tetrahydrofuran / -78 - 20 °C / Inert atmosphere

4: carbon tetrabromide; triethylamine; triphenylphosphine / dichloromethane / 2 h / 0 °C

With carbon tetrabromide; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/j.tet.2011.12.063

upstream raw materials:

C₂₅H₂₇NO₃

(2R,3R,4R)-3,4-bis(benzyloxy)-tetrahydrofuran-2-ol

(2R,3S,4S)-4-(benzylamino)-2,3-bis(benzyloxy)-8-(tert-butyldimethylsilyloxy)octan-1-ol

benzyl bromide

Downstream raw materials:

4-[(2S,3S,4R)-1-benzyl-3,4-bis(benzyloxy)pyrrolidin-2-yl]butan-1-ol

(1S,2R,8aS)-1,2-bis(benzyloxy)octahydroindolizine

(-)-2-epi-lentiginosine