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

Base Information

• Chemical Name: (2S,3S,4S)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-isopropylidenylpyrrolidine
• CAS No.: 267244-43-9
• Molecular Formula: C₂₅H₃₅NO₅
• Molecular Weight: 429.557
• Mol file: 267244-43-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (2S,3S,4S)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-isopropylidenylpyrrolidine 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:

benzoyl chloride (98-88-4) + 3-tert-butoxycarbonylmethyl-4-isopropenyl-pyrrolidine-2-carboxylic acid tert-butyl ester → (2S,3S,4S)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-isopropylidenylpyrrolidine (267244-43-9)

Guidance literature:

With sodium hydroxide;

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

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:

(2S,3S,4S)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-isopropylidenylpyrrolidine (267244-43-9) → (2S,3S,4S)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-(quinoxal-2'-yl)pyrrolidine (339557-52-7)

Guidance literature:

Multi-step reaction with 5 steps

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

1.2: 99 percent / Ph₃P / CH₂Cl₂; methanol / 1 h / 20 °C

2.1: lithium hexamethyldisilylamide / tetrahydrofuran / 0.42 h / -78 °C

3.1: 115 mg / phenyltrimethylammonium tribromide / tetrahydrofuran / 0.5 h / 0 °C

4.1: NaHCO₃ / ethanol / 7 h / Heating

5.1: 26.0 mg / Pd/C / ethanol / 3 h / Heating

With phenyltrimethylammonium tribromide; sodium hydrogencarbonate; ozone; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane;

DOI:10.1021/jo000846l

upstream raw materials:

benzoyl chloride

Downstream raw materials:

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

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

(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