(2S,4R)-N-(benzyloxycarbonyl)-2-t-butyldimethylsilyloxymethyl-4-oxyacetylpyrrolidine

Base Information

• Chemical Name: (2S,4R)-N-(benzyloxycarbonyl)-2-t-butyldimethylsilyloxymethyl-4-oxyacetylpyrrolidine
• CAS No.: 864755-02-2
• Molecular Formula: C₂₁H₃₃NO₅Si
• Molecular Weight: 407.582
• Mol file: 864755-02-2.mol

Synonyms:(2S,4R)-N-(benzyloxycarbonyl)-2-t-butyldimethylsilyloxymethyl-4-oxyacetylpyrrolidine

Chemical Property of (2S,4R)-N-(benzyloxycarbonyl)-2-t-butyldimethylsilyloxymethyl-4-oxyacetylpyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-N-(benzyloxycarbonyl)-2-t-butyldimethylsilyloxymethyl-4-oxyacetylpyrrolidine

There total 1 articles about (2S,4R)-N-(benzyloxycarbonyl)-2-t-butyldimethylsilyloxymethyl-4-oxyacetylpyrrolidine 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: 96.0%

acetic anhydride (108-24-7) + benzyl (2S,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-hydroxypyrrolidine-1-carboxylate (260417-93-4) → (2S,4R)-N-(benzyloxycarbonyl)-2-t-butyldimethylsilyloxymethyl-4-oxyacetylpyrrolidine (864755-02-2)

Guidance literature:

With pyridine; dmap; In tetrahydrofuran; for 16h;

Reference yield:

(2S,4R)-N-(benzyloxycarbonyl)-2-t-butyldimethylsilyloxymethyl-4-oxyacetylpyrrolidine (864755-02-2) → 1,1'-[[(pentane-1,5-diyl)dioxy]bis[(2S,4R)-[5-methoxy-1,4-phenylene-2-(2,2,2-trichloroethoxycarbonylamino)]carbonyl]]bis[2-hydroxymethyl-4-hydroxyacetylpyrrolidine] (913262-33-6)

Guidance literature:

Multi-step reaction with 5 steps

1: hydrogen / palladium 10% on activated carbon / ethanol / 16 h / 2327.23 Torr

2: triethylamine / tetrahydrofuran / 16 h / 0 - 20 °C

3: hydrogen / palladium 10% on activated carbon / ethyl acetate / 24 h / 1551.49 Torr

4: pyridine / dichloromethane / 16 h / -10 - 20 °C

5: water; acetic acid / tetrahydrofuran / 16 h / 20 °C

With pyridine; water; hydrogen; acetic acid; triethylamine; palladium 10% on activated carbon; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate;

Reference yield:

(2S,4R)-N-(benzyloxycarbonyl)-2-t-butyldimethylsilyloxymethyl-4-oxyacetylpyrrolidine (864755-02-2) → 1,1'-[[(pentane-1,5-diyl)dioxy]bis[(2S,4R)-[5-methoxy-1,4-phenylene-2-(2,2,2-trichloroethoxycarbonylamino)]carbonyl]]bis[2-(tert-butyldimethylsilyloxymethyl)-4-hydroxyacetylpyrrolidine] (913262-32-5)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogen / palladium 10% on activated carbon / ethanol / 16 h / 2327.23 Torr

2: triethylamine / tetrahydrofuran / 16 h / 0 - 20 °C

3: hydrogen / palladium 10% on activated carbon / ethyl acetate / 24 h / 1551.49 Torr

4: pyridine / dichloromethane / 16 h / -10 - 20 °C

With pyridine; hydrogen; triethylamine; palladium 10% on activated carbon; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate;

upstream raw materials:

acetic anhydride

benzyl (2S,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-hydroxypyrrolidine-1-carboxylate

Downstream raw materials:

1,1'-[[(propane-1,3-diyl)dioxy]bis[(2S,4R)-(5-methoxy-2-amino-1,4-phenylene)carbonyl]]bis[2-(tert-butyldimethylsilyloxymethyl)-4-oxyacetylpyrrolidine]

1,1'-[[(propane-1,3-diyl)dioxy]bis[(2S,4R)-(5-methoxy-2-nitro-1,4-phenylene)carbonyl]]bis[2-(tert-butyldimethylsilyloxymethyl)-4-oxyacetylpyrrolidine]

1,1'-[[(propane-1,3-diyl)dioxy]bis[(2S,4R)-[5-methoxy-1,4-phenylene-2-(2,2,2-trichloroethoxycarbonylamino)]carbonyl]]bis(2-hydroxymethyl-4-oxyacetylpyrrolidine)

1,1'-[[(propane-1,3-diyl)dioxy]bis[(2S,4R)-[5-methoxy-1,4-phenylene-2-(2,2,2-trichloroethoxycarbonylamino)]carbonyl]]bis[2-(tert-butyldimethylsilyloxymethyl)-4-oxyacetylpyrrolidine]