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

Base Information

• Chemical Name: (2S,3S,5S)-3-Acetoxy-5-(allyl-dimethyl-silanylmethyl)-2-benzyl-pyrrolidine-1-carboxylic acid benzyl ester
• CAS No.: 637338-15-9
• Molecular Formula: C₂₇H₃₅NO₄Si
• Molecular Weight: 465.665
• Mol file: 637338-15-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (2S,3S,5S)-3-Acetoxy-5-(allyl-dimethyl-silanylmethyl)-2-benzyl-pyrrolidine-1-carboxylic acid benzyl ester 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: 85.0%

acetic anhydride (108-24-7) + (2S,3S,5S)-5-(Allyl-dimethyl-silanylmethyl)-2-benzyl-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester (637338-14-8) → (2S,3S,5S)-3-Acetoxy-5-(allyl-dimethyl-silanylmethyl)-2-benzyl-pyrrolidine-1-carboxylic acid benzyl ester (637338-15-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1055/s-2003-41433

Reference yield:

(2S,3S,5S)-3-Acetoxy-5-(allyl-dimethyl-silanylmethyl)-2-benzyl-pyrrolidine-1-carboxylic acid benzyl ester (637338-15-9) → (2S,3S,5S)-3-Acetoxy-2-benzyl-5-(fluoro-dimethyl-silanylmethyl)-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:

(2S,3S,5S)-3-Acetoxy-5-(allyl-dimethyl-silanylmethyl)-2-benzyl-pyrrolidine-1-carboxylic acid benzyl ester; With bromine; In dichloromethane;

With pyridine hydrogenfluoride; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1055/s-2003-41433

Reference yield:

(2S,3S,5S)-3-Acetoxy-5-(allyl-dimethyl-silanylmethyl)-2-benzyl-pyrrolidine-1-carboxylic acid benzyl ester (637338-15-9) → (2S,3S,5S)-2-Benzyl-3-hydroxy-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:

Multi-step reaction with 3 steps

1.1: Br₂ / CH₂Cl₂

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

2.1: 286 mg / KHCO₃; KF; aq. H₂O₂ / tetrahydrofuran; methanol / 10 h / 20 °C

3.1: KOH

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

DOI:10.1055/s-2003-41433

upstream raw materials:

acetic anhydride

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

Downstream raw materials:

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