benzyl (2S,4S,5R)-4-acetoxy-2-carboxy-5-[(tert-butyldimethylsilyloxy)methyl]pyrrolidine-1-carboxylate

Base Information

• Chemical Name: benzyl (2S,4S,5R)-4-acetoxy-2-carboxy-5-[(tert-butyldimethylsilyloxy)methyl]pyrrolidine-1-carboxylate
• CAS No.: 337975-48-1
• Molecular Formula: C₂₂H₃₃NO₇Si
• Molecular Weight: 451.592
• Mol file: 337975-48-1.mol

Synonyms:benzyl (2S,4S,5R)-4-acetoxy-2-carboxy-5-[(tert-butyldimethylsilyloxy)methyl]pyrrolidine-1-carboxylate

Chemical Property of benzyl (2S,4S,5R)-4-acetoxy-2-carboxy-5-[(tert-butyldimethylsilyloxy)methyl]pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2S,4S,5R)-4-acetoxy-2-carboxy-5-[(tert-butyldimethylsilyloxy)methyl]pyrrolidine-1-carboxylate

There total 14 articles about benzyl (2S,4S,5R)-4-acetoxy-2-carboxy-5-[(tert-butyldimethylsilyloxy)methyl]pyrrolidine-1-carboxylate 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:

Acetic acid (2R,3S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxymethyl-pyrrolidin-3-yl ester → benzyl (2S,4S,5R)-4-acetoxy-2-carboxy-5-[(tert-butyldimethylsilyloxy)methyl]pyrrolidine-1-carboxylate (337975-48-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / aq. NaHCO₃ / CH₂Cl₂ / 20 °C

2: 80 percent / NaIO₄ / RuCl₃ / acetonitrile; CCl₄; H₂O / 0 °C

With sodium periodate; sodium hydrogencarbonate; ruthenium trichloride; In tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(01)00071-5

Reference yield:

Benzyl-[(1R,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-3-oxiranyl-propyl]-carbamic acid benzyl ester → benzyl (2S,4S,5R)-4-acetoxy-2-carboxy-5-[(tert-butyldimethylsilyloxy)methyl]pyrrolidine-1-carboxylate (337975-48-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / pyridine; DMAP / 20 °C

2: H₂ / Pd/C / methanol / 20 °C

3: 65 percent / aq. NaHCO₃ / CH₂Cl₂ / 20 °C

4: 80 percent / NaIO₄ / RuCl₃ / acetonitrile; CCl₄; H₂O / 0 °C

With pyridine; dmap; sodium periodate; hydrogen; sodium hydrogencarbonate; ruthenium trichloride; palladium on activated charcoal; In methanol; tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(01)00071-5

Reference yield:

Acetic acid (1S,2R)-2-(benzyl-benzyloxycarbonyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-1-oxiranylmethyl-propyl ester (337975-51-6) → benzyl (2S,4S,5R)-4-acetoxy-2-carboxy-5-[(tert-butyldimethylsilyloxy)methyl]pyrrolidine-1-carboxylate (337975-48-1)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / Pd/C / methanol / 20 °C

2: 65 percent / aq. NaHCO₃ / CH₂Cl₂ / 20 °C

3: 80 percent / NaIO₄ / RuCl₃ / acetonitrile; CCl₄; H₂O / 0 °C

With sodium periodate; hydrogen; sodium hydrogencarbonate; ruthenium trichloride; palladium on activated charcoal; In methanol; tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(01)00071-5

upstream raw materials:

Acetic acid (1S,2R)-2-(benzyl-benzyloxycarbonyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-1-oxiranylmethyl-propyl ester

N-(benzyloxycarbonyl)-D-serine

(R)-benzyl 3-hydroxy-1-(methoxy(methyl)amino)-1-oxopropane-2-ylcarbamate

(R)-benzyl-4-(methoxy(methyl)carbamoyl)-2,2-dimethyloxazolidine-3-carboxylate

Downstream raw materials:

C₂₆H₃₆N₂O₉Si

(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)pyrrolidine-2-carboxylic acid

(2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester