(2S,3S,5S)-3-acetyl-2-benzyl-benzyloxycarbonyl-5-hydroxymethyl-pyrrolidine

Base Information

• Chemical Name: (2S,3S,5S)-3-acetyl-2-benzyl-benzyloxycarbonyl-5-hydroxymethyl-pyrrolidine
• CAS No.: 637338-16-0
• Molecular Formula: C₂₂H₂₅NO₅
• Molecular Weight: 383.444
• Mol file: 637338-16-0.mol

Synonyms:(2S,3S,5S)-3-acetyl-2-benzyl-benzyloxycarbonyl-5-hydroxymethyl-pyrrolidine

Chemical Property of (2S,3S,5S)-3-acetyl-2-benzyl-benzyloxycarbonyl-5-hydroxymethyl-pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,5S)-3-acetyl-2-benzyl-benzyloxycarbonyl-5-hydroxymethyl-pyrrolidine

There total 4 articles about (2S,3S,5S)-3-acetyl-2-benzyl-benzyloxycarbonyl-5-hydroxymethyl-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:

(2S,3S,5S)-3-Acetoxy-2-benzyl-5-(fluoro-dimethyl-silanylmethyl)-pyrrolidine-1-carboxylic acid benzyl ester → (2S,3S,5S)-3-acetyl-2-benzyl-benzyloxycarbonyl-5-hydroxymethyl-pyrrolidine (637338-16-0)

Guidance literature:

With potassium fluoride; dihydrogen peroxide; potassium hydrogencarbonate; In tetrahydrofuran; methanol; at 20 ℃; for 10h;

DOI:10.1055/s-2003-41433

Reference yield:

benzyl (1S)-(1-formyl-2-phenylethyl)carbamate (59830-60-3) → (2S,3S,5S)-3-acetyl-2-benzyl-benzyloxycarbonyl-5-hydroxymethyl-pyrrolidine (637338-16-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: BF₃*OEt₂ / CH₂Cl₂ / 0.33 h / -10 °C

1.2: 70 percent / CH₂Cl₂ / 2 h / -10 °C

2.1: 85 percent / Et₃N; DMAP / CH₂Cl₂ / 4 h / 20 °C

3.1: Br₂ / CH₂Cl₂

3.2: HF*pyridine / CH₂Cl₂ / 3 h / 20 °C

4.1: 286 mg / KHCO₃; KF; aq. H₂O₂ / tetrahydrofuran; methanol / 10 h / 20 °C

With dmap; potassium fluoride; boron trifluoride diethyl etherate; dihydrogen peroxide; bromine; potassium hydrogencarbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1055/s-2003-41433

Reference yield:

(2S,3S,5S)-5-(Allyl-dimethyl-silanylmethyl)-2-benzyl-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester (637338-14-8) → (2S,3S,5S)-3-acetyl-2-benzyl-benzyloxycarbonyl-5-hydroxymethyl-pyrrolidine (637338-16-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 85 percent / Et₃N; DMAP / CH₂Cl₂ / 4 h / 20 °C

2.1: Br₂ / CH₂Cl₂

2.2: HF*pyridine / CH₂Cl₂ / 3 h / 20 °C

3.1: 286 mg / KHCO₃; KF; aq. H₂O₂ / tetrahydrofuran; methanol / 10 h / 20 °C

With dmap; potassium fluoride; dihydrogen peroxide; bromine; potassium hydrogencarbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1055/s-2003-41433

upstream raw materials:

benzyl (1S)-(1-formyl-2-phenylethyl)carbamate

(2S,3S,5S)-5-(Allyl-dimethyl-silanylmethyl)-2-benzyl-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

(2S,3S,5S)-3-Acetoxy-5-(allyl-dimethyl-silanylmethyl)-2-benzyl-pyrrolidine-1-carboxylic acid benzyl ester