(2S,3S,4S)-acetyl-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-pyrrolidine

Base Information

• Chemical Name: (2S,3S,4S)-acetyl-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-pyrrolidine
• CAS No.: 267244-44-0
• Molecular Formula: C₂₄H₃₃NO₆
• Molecular Weight: 431.529
• Mol file: 267244-44-0.mol

Synonyms:(2S,3S,4S)-acetyl-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-pyrrolidine

Chemical Property of (2S,3S,4S)-acetyl-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S)-acetyl-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-pyrrolidine

There total 3 articles about (2S,3S,4S)-acetyl-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-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: 99.0%

(2S,3S,4S)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-isopropylidenylpyrrolidine (267244-43-9) → (2S,3S,4S)-acetyl-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-pyrrolidine (267244-44-0)

Guidance literature:

(2S,3S,4S)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-isopropylidenylpyrrolidine; With ozone; In methanol; dichloromethane; at -78 ℃;

With triphenylphosphine; In methanol; dichloromethane; at -78 - 20 ℃;

DOI:10.1016/S0960-894X(99)00690-3

Reference yield:

benzoyl chloride (98-88-4) → (2S,3S,4S)-acetyl-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-pyrrolidine (267244-44-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 455 mg / NaOH / H₂O; dioxane / 22 h / 20 °C

2.1: O₃ / CH₂Cl₂; methanol / 0.75 h / -78 °C

2.2: 99 percent / Ph₃P / CH₂Cl₂; methanol / 1 h / 20 °C

With sodium hydroxide; ozone; In 1,4-dioxane; methanol; dichloromethane; water;

DOI:10.1021/jo000846l

Reference yield:

3-tert-butoxycarbonylmethyl-4-isopropenyl-pyrrolidine-2-carboxylic acid tert-butyl ester → (2S,3S,4S)-acetyl-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-pyrrolidine (267244-44-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 455 mg / NaOH / H₂O; dioxane / 22 h / 20 °C

2.1: O₃ / CH₂Cl₂; methanol / 0.75 h / -78 °C

2.2: 99 percent / Ph₃P / CH₂Cl₂; methanol / 1 h / 20 °C

With sodium hydroxide; ozone; In 1,4-dioxane; methanol; dichloromethane; water;

DOI:10.1021/jo000846l

upstream raw materials:

(2S,3S,4S)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-isopropylidenylpyrrolidine

benzoyl chloride

Downstream raw materials:

(2S,3S,4S)-N-benzoyl-4-(bromoacetyl)-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethylpyrrolidine

1-benzoyl-3-tert-butoxycarbonylmethyl-4-(1-trimethylsilanyloxy-vinyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

(2S,3S,4S)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-(2'-methylthiazol-4'-yl)pyrrolidine

(2S,3S,4S)-4-(2'-aminothiazol-4'-yl)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethylpyrrolidine