129740-14-3

Basic information

• Product Name: L-AZETIDINE-2-CARBOXYLIC ACID T-BUTYL ESTER
• Synonyms: L-AZETIDINE-2-CARBOXYLIC ACID T-BUTYL ESTER;(2S)-2-Azetidinecarboxylic Acid 1,1-DiMethylethyl Ester;2-Azetidinecarboxylic acid, 1,1-diMethylethyl ester, (2S)-
• CAS NO: 129740-14-3
• Molecular Formula: C₈H₁₅NO₂
• Molecular Weight: 157.2102
• Product Categories: Amino Acids 13C, 2H, 15N;Amino Acids & Derivatives
• Mol File: 129740-14-3.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform, Dichloromethane, Methanol
• CAS DataBase Reference: L-AZETIDINE-2-CARBOXYLIC ACID T-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: L-AZETIDINE-2-CARBOXYLIC ACID T-BUTYL ESTER(129740-14-3)
• EPA Substance Registry System: L-AZETIDINE-2-CARBOXYLIC ACID T-BUTYL ESTER(129740-14-3)

Safety Data

• Hazardous Substances Data: 129740-14-3(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

Uses

L-Azetidine-2-carboxylic Acid t-Butyl Ester is a protected four-membered ring analog of L-Proline,it is a useful intermediate in the synthesis of polypeptides.

Upstream product

• 161370-66-7 (2S)-2-(tert-butoxycarbonyl)amino-4-iodobutanoic acid tert-butyl ester 
• 81323-58-2 N-(tert-butyloxycarbonyl)-(S)-homoserine tert-butyl ester 
• 34582-32-6 N-tert-butoxycarbonyl aspartic acid tert-butyl ester 
• 1173708-25-2 SES-Aze-OtBu 
• 153704-88-2 (S)-1-benzyl 2-tert-butyl azetidine-1,2-dicarboxylate 

Downstream Products

• 201283-56-9 (2S,3S,3''S)-N-[3-(3-acetoxy-3-methoxycarbonylpropanamido)-3-t-butoxycarbonylpropanoyl]azetidine-2-carboxylic acid t-butyl ester 
• 2133-34-8 (2S)-azetidine-2-carboxylic acid 
• 1235453-07-2 tert-butyl (2S,3'S)-1-(3'-benzyloxycarbonylamino-4'-tert-butoxy-4'-oxobutyl)azetidine-2-carboxylate 

Relevant articles and documents

Direct access to L-azetidine-2-carboxylic acid

A straightforward synthesis of L-azetidine-2-carboxylic acid is described, leading to both orthogonally protected versions or totally deprotected L-Aze. The starting material is a commercially available aspartic acid derivative, whose chirality is conserv

Ring-Strain Effects in Base-Induced Sommelet–Hauser Rearrangement: Application to Successive Stereocontrolled Transformations

The base-induced Sommelet–Hauser (S–H) rearrangement of azetidine-2-carboxylic acid ester-derived ammonium salts into 2-aryl-substituted derivatives was demonstrated. The ring-strain of four-membered N-heterocycles enables efficient generation of the desired ylide intermediate and enhances the rate of the S–H rearrangement. The asymmetric version of the rearrangement was characterized by excellent levels of successive chirality transmissions. The regio- and stereo-controlled nucleophilic ring opening of the rearrangement products produced quaternary α-aryl amino acid esters with excellent enantiopurities.

Total Synthesis of Mugineic Acid. Efficient Use of the Phenyl Group as the Carboxyl Synthon

Stereoselective total synthesis of mugineic acid (1), a unique phytosiderophore from roots of barley, has been achieved from readily available (2S,3S)- and (2R,3R)-2,3-epoxycinnamyl alcohols (5) and (6).The key step is the oxidation of the phenyl group to the carboxylic acid by use of the ruthenium trichloride-sodium metaperiodate system.