Production Method 1

81658-26-6

81658-25-5

Reaction Conditions

1.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran

Reference

Synthesis of (3R,4R,5R)-1-(tert-butoxycarbonyl)-3,4-isopropylidenedioxy-5-methoxymethyl-2-pyrrolidinone from (S)-pyroglutaminol

Ikota, Nobuo, Chemical & Pharmaceutical Bulletin, 1992, 40(7), 1925-7

Production Method 2

53100-44-0

81658-25-5

Reaction Conditions

1.1 Reagents: Triethylamine ,  Ethyl chloroformate Solvents: Tetrahydrofuran ;  -10 °C
1.2 Reagents: Sodium borohydride Solvents: Ethanol ;  -10 °C

Reference

Total synthesis of (-)-domoic acid. A revision of the original structure

Ohfune, Yasufumi; Tomita, Masako, Journal of the American Chemical Society, 1982, 104(12), 3511-13

Production Method 3

81658-26-6

81658-25-5

Reaction Conditions

1.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran

Reference

Unprecedented Migration of N-Alkoxycarbonyl Groups in Protected Pyroglutaminol

Bunch, Lennart; Norrby, Per-Ola; Frydenvang, Karla; Krogsgaard-Larsen, Povl; Madsen, Ulf, Organic Letters, 2001, 3(3), 433-435

tert-Butyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate Raw materials

• (2S)-N-(tert-Butyloxycarbonyl)-O-(tert-butyl)dimethylsilyl-pyroglutaminol
• Boc-pyr-OH

tert-Butyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate Preparation Products

• tert-Butyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate (81658-25-5)

• 1. Establishing empirical design rules of nucleic acid templates for the synthesis of silver nanoclusters with tunable photoluminescence and functionalities towards targeted bioimaging applications?
  Jason Y. C. Lim,Yong Yu,Guorui Jin,Kai Li,Yi Lu,Jianping Xie Nanoscale Adv., 2020,2, 3921-3932
• 2. Excellent energy storage performance in NaNbO3-based relaxor antiferroeic ceramics under a low electric field
  XuxinCheng,XiaomingChen,PengyuanFan
• 3. Fe/S-Catalyzed synthesis of 2-benzoylbenzoxazoles and 2-quinolylbenzoxazoles via redox condensation of o-nitrophenols with acetophenones and methylquinolines?
  Thi Thu Tram Nguyen,Thanh Binh Nguyen Org. Biomol. Chem., 2021,19, 6015-6020
• 4. Fate of nitrogen-15 in the subsequent growing season of greenhouse tomato plants (Lycopersicon esculentum Mill) as influenced by alternate partial root-zone irrigation
  Maomao Hou,Fenglin Zhong,Qiu Jin,Enjiang Liu,Jie Feng,Tengyun Wang,Yue Gao RSC Adv., 2017,7, 34392-34400
• 5. Establishing the accuracy of position-specific carbon isotope analysis of propane by GC-pyrolysis-GC-IRMS
  ChangjieLiu,PengLiu,XiaofengWang,XiaoqiangLi,JuskeHorita

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrrolidines Pyrrolidones Oxoprolines
• Solvents and Organic Chemicals Organic Compounds Alcohol/Ether

tert-Butyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate: A Comprehensive Overview

The compound with CAS No 81658-25-5, commonly referred to as tert-butyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate, is a significant molecule in the field of organic chemistry and pharmaceutical research. This compound is characterized by its unique structure, which includes a tert-butyl group, a pyrrolidine ring, and a carboxylic acid derivative. The stereochemistry at the second carbon of the pyrrolidine ring, denoted by the (2S) configuration, plays a crucial role in its biological activity and synthetic applications.

Recent studies have highlighted the importance of tert-butyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate in drug discovery and development. Its structure makes it an ideal candidate for exploring enzyme inhibition, particularly in the context of protease inhibitors. Researchers have demonstrated that this compound exhibits potential inhibitory activity against certain proteases, which are key targets in treating viral infections and neurodegenerative diseases. The tert-butyl group contributes to the molecule's stability, while the hydroxymethyl substituent enhances its ability to interact with biological targets.

In terms of synthesis, tert-butyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate is typically prepared through a multi-step process involving asymmetric induction techniques. The use of chiral catalysts has enabled the selective formation of the (2S) enantiomer, which is critical for its desired pharmacological properties. This compound serves as an intermediate in the synthesis of more complex molecules, including those with potential therapeutic applications.

The application of tert-butyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate extends beyond pharmaceuticals. It has also been explored in materials science for its ability to form self-assembled structures under specific conditions. These structures exhibit unique physical properties, making them suitable for applications in nanotechnology and drug delivery systems.

From an analytical perspective, the characterization of tert-butyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate has been enhanced by advanced spectroscopic techniques such as NMR and mass spectrometry. These methods provide detailed insights into the molecule's conformational dynamics and stereochemical integrity, which are essential for understanding its behavior in different environments.

In conclusion, tert-butyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate is a versatile compound with significant potential in both academic research and industrial applications. Its unique structure, coupled with recent advancements in synthetic and analytical methodologies, positions it as a valuable tool in the development of novel therapeutics and materials.

• 2389-45-9((S)-6-(((Benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)hexanoic acid)
• 2043-21-2(3-Acryloyl-2-oxazolidinone)
• 160347-90-0((2R)-1-[(tert-butoxy)carbonyl]-5-oxopyrrolidine-2-carboxylic acid)
• 1148-11-4(Carbobenzoxyproline)
• 128811-37-0(tert-Butyl (2R)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate)
• 2018-66-8(N-Cbz-L-leucine)
• 1432-43-5(3-Acetyl-2-oxazolidinone)
• 2212-76-2(Z-Lys(boc)-oh dcha)
• 695-53-4(5,5-dimethyl-1,3-oxazolidine-2,4-dione)
• 53100-44-0(Boc-pyr-OH)