L-Azetidine-2-carboxylic Acid t-Butyl Ester

Base Information

• Chemical Name: L-Azetidine-2-carboxylic Acid t-Butyl Ester
• CAS No.: 129740-14-3
• Molecular Formula: C8H15NO2
• Molecular Weight: 157.213
• DSSTox Substance ID: DTXSID50447143
• Nikkaji Number: J1.503.990F
• Wikidata: Q82265951
• Mol file: 129740-14-3.mol

Synonyms:129740-14-3;L-Azetidine-2-carboxylic Acid t-Butyl Ester;Tert-butyl (2S)-azetidine-2-carboxylate;(S)-tert-Butyl azetidine-2-carboxylate;(2S)-2-Boc-azetidine;SCHEMBL7359958;DTXSID50447143;MFCD09835146;(S)-tert-Butylazetidine-2-carboxylate;AKOS006327291;t-Butyl (2S)-azetidine-2-carboxylate;PS-17188;CS-0057009;D84842;EN300-6510269;(S)-Azetidine-2-carboxylic acid tert-butyl ester;J-005709

Chemical Property of L-Azetidine-2-carboxylic Acid t-Butyl Ester

Chemical Property:

• PSA: 38.33000
• LogP: 1.01880
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform, Dichloromethane, Methanol
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 157.110278721
• Heavy Atom Count: 11
• Complexity: 160

Purity/Quality:

99% ^*data from raw suppliers

L-Azetidine-2-carboxylic Acid t-Butyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C1CCN1
• Isomeric SMILES: CC(C)(C)OC(=O)[C@@H]1CCN1
• 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.

Technology Process of L-Azetidine-2-carboxylic Acid t-Butyl Ester

There total 9 articles about L-Azetidine-2-carboxylic Acid t-Butyl 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: 99.0%

(S)-1-benzyl 2-tert-butyl azetidine-1,2-dicarboxylate (153704-88-2) → tert-butyl (2S)-azetidine-2-carboxylate (129740-14-3,208034-97-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 1h; Ambient temperature;

DOI:10.1016/S0040-4020(01)88039-X

Reference yield: 75.0%

SES-Aze-OtBu (1173708-25-2) → tert-butyl (2S)-azetidine-2-carboxylate (129740-14-3,208034-97-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1002/ejoc.200900233

Reference yield: 68.0%

tert-butyl N-(p-toluenesulfonyl)-(S)-azetidine-2-carboxylate → tert-butyl (2S)-azetidine-2-carboxylate (129740-14-3,208034-97-3)

Guidance literature:

With methanol; magnesium; at 0 - 20 ℃; for 2h;

DOI:10.3987/COM-18-14002

upstream raw materials:

(S)-1-benzyl 2-tert-butyl azetidine-1,2-dicarboxylate

SES-Aze-OtBu

N-tert-butoxycarbonyl aspartic acid tert-butyl ester

N-(tert-butyloxycarbonyl)-(S)-homoserine tert-butyl ester

Downstream raw materials:

(2S)-azetidine-2-carboxylic acid

tert-butyl (2S,3'S)-1-(3'-benzyloxycarbonylamino-4'-tert-butoxy-4'-oxobutyl)azetidine-2-carboxylate

(2S,3S,3''S)-N-[3-(3-acetoxy-3-methoxycarbonylpropanamido)-3-t-butoxycarbonylpropanoyl]azetidine-2-carboxylic acid t-butyl ester

Refernces

• 1、 Takaishi, Tomohiro,Wakisaka, Kyosuke,Vavricka, Christopher J.,Kiyota, Hiromasa,Izumi, Minoru. "Multigram-scale and column chromatography-free synthesis of L-azetidine-2-carboxylic acid for the synthesis of nicotianamine and its derivatives". . p. 2126 - 2134. Retrieved 2019/04/04.
• 2、 Klair, Sukhbinder S.,Mohan, Hindupur R.,Kitahara, Takeshi. "A novel synthetic approach towards phytosiderophores: Expeditious synthesis of nicotianamine and 2'-deoxymugineic acid". . p. 89 - 92. Retrieved 2007/10/03.