86661-32-7

Usage

Uses

Used in Pharmaceutical Industry:
(S)-tert-Butyl 2-(tosyloxymethyl)pyrrolidine-1-carboxylate is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its role in this industry is crucial due to its ability to contribute to the development of new drugs and medicines, enhancing the therapeutic options available to patients.
Used in Chemical Industry:
In the chemical industry, (S)-tert-Butyl 2-(tosyloxymethyl)pyrrolidine-1-carboxylate is utilized as a key component in the production of other organic compounds. Its stability and versatility make it an ideal candidate for use in a wide range of chemical processes, contributing to the creation of diverse chemical products.
Used as a Chiral Building Block:
(S)-tert-Butyl 2-(tosyloxymethyl)pyrrolidine-1-carboxylate is employed as a chiral building block in organic synthesis. Its chiral nature is essential for the creation of enantiomerically pure compounds, which are critical in various applications, including the development of pharmaceuticals with specific biological activities.
Used with Protecting Groups in Organic Synthesis:
The tosyloxymethyl group in (S)-tert-Butyl 2-(tosyloxymethyl)pyrrolidine-1-carboxylate serves as a protecting group, which is used to selectively modify the reactivity of certain functional groups in organic synthesis. This selective protection allows for more controlled and precise chemical reactions, leading to the production of desired compounds with greater accuracy and efficiency.

InChI:InChI=1/C17H25NO5S/c1-13-7-9-15(10-8-13)24(20,21)22-12-14-6-5-11-18(14)16(19)23-17(2,3)4/h7-10,14H,5-6,11-12H2,1-4H3/t14-/m0/s1

Upstream product

• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 84890-94-8 (S)-2-Isobutoxycarbonyloxycarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 98-59-9 p-toluenesulfonyl chloride 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 616-47-7 1-methyl-1H-imidazole 
• 135097-23-3 (2S)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 147-85-3 L-proline 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 876617-06-0 tert-butyl (2R)-2-ethylpyrrolidine-1-carboxylate 
• 73236-85-8 (S)-2-<(acetylthio)methyl>-1-<(tert-butyloxy)carbonyl>pyrrolidine 
• 53310-83-1 (S)-tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one 
• 77489-32-8 Boc-ProψGly-OH 
• 135055-75-3 (S)-(-)-N-tert-butoxycarbonyl-2-<(diphenylphosphino)methyl>pyrrolidine 
• 142253-50-7 (S)-2-cyanomethylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 224620-23-9 (S)-(-)-N-tert-butoxycarbonyl-2-<(bis(4-N,N-dimethylaminophenyl)phosphino)methyl>pyrrolidine 
• 118656-45-4 tert-butyl (2S)-2-[(phenylsulfanyl)methyl]pyrrolidine-1-carboxylate 
• 224620-22-8 (S)-(-)-N-tert-butoxycarbonyl-2-<(bis(4-methoxyphenyl)phosphino)methyl>pyrrolidine 
• 224784-84-3 (S)-(+)-N-tert-butoxycarbonyl-2-<(N',N'-diphenylamino)methyl>pyrrolidine 
• 174213-51-5 (S)-tert-butyl 2-(phenoxymethyl)pyrrolidine-1-carboxylate 
• 168049-26-1 tert-butyl (2S)-2-(azidomethyl)-1-pyrrolidinecarboxylate 
• 622411-10-3 methyl 2-amino-5{{(2S)-1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl}methoxy}benzoate 
• 922529-41-7 1-(tert-butoxycarbonyl)-(2S)-pyrrolidinylmethyl 4-iodophenyl sulfide 

Relevant academic research and scientific papers

PYRAZOLE AND IMIDAZOLE DERIVATIVES, COMPOSITIONS AND METHODS AS OREXIN ANTAGONISTS

The present invention is directed to substituted Pyrazole and Imidazole derivatives of compounds that are antagonists of orexin receptors, and which are useful in the treatment or prevention of neurological and psychiatric disorders and diseases in which

IMIDAZOLO DERIVATIVES, COMPOSITIONS AND METHODS AS OREXIN ANTAGONISTS

This disclosure is directed to substituted Imidazolo[2,1-b]oxazole, lmidazolo[2,1-b]thiazole, Imidazolo[2,1-b]oxadiazole, lmidazolo[2,1-b]oxadiathiazole derivatives of compounds that are antagonists of orexin receptors, and which are useful in the treatme

Chiral phosphine nitrogen phosphine ligand and chiral metal organic coordination complex and application

The invention discloses a chiral phosphine nitrogen phosphine ligand and chiral metal organic coordination complex and application. The chiral tridentate phosphine nitrogen phosphine ligand is shown as a formula (I), and the chiral metal organic coordination complex is shown as a formula (II), wherein the chiral metal organic coordination complex shown as the formula (II) is used as a homogeneouscatalyst to be applied to preparation of phenylalanine derivatives with high optical activity. The novel chiral nitrogen-phosphine ligand synthesized by taking cheap amino acid as a chiral source is applied to asymmetric hydrogenation reaction, and a chiral product with relatively high yield can be obtained with relatively low catalytic dosage, relatively short reaction time and relatively mild reaction conditions.

Efficient synthesis, biological evaluation, and docking study of isatin based derivatives as caspase inhibitors

ABTRACT: In this paper, a new series of isatin-sulphonamide based derivatives were designed, synthesised and evaluated as caspase inhibitors. The compounds containing 1-(pyrrolidinyl)sulphonyl and 2-(phenoxymethyl)pyrrolidin-1-yl)sulphonyl substitution at C5 position of isatin core exhibited better results compared to unsubstituted derivatives. According to the results of caspase inhibitory activity, compound 20d showed moderate inhibitory activity against caspase-3 and ?7 in?vitro compared to Ac-DEVD-CHO (IC50 = 0.016 ± 0.002 μM). Among the studied compounds, some active inhibitors with IC50s in the range of 2.33–116.91 μM were identified. The activity of compound 20d was rationalised by the molecular modelling studies exhibiting the additional van der Waals interaction of N-phenylacetamide substitution along with efficacious T-shaped π-π and pi-cation interactions. The introduction of compound 20d with good caspase inhibitory activity will help researchers to find more potent agents.

Synthesis and Stereochemical Assignment of Conioidine A: DNA- And HSA-Binding Studies of the Four Diastereomers

Conioidine A (1), isolated in 1993 with unknown relative and absolute configuration, was suggested to be a DNA-binding compound by an indirect technique. Four stereoisomers of conioidine A have been synthesized from d- and l-proline, and the natural product has been identified as possessing (4R,6R) absolute configuration. Binding of the conioidine diastereomers to calf thymus DNA (CT DNA) and human serum albumin (HSA) has been investigated by fluorescence spectroscopy and isothermal titration calorimetry (ITC). All stereoisomers display at least an order of magnitude weaker binding to DNA than the control compound netropsin; however, a strong association with HSA was observed for the (4R,6S) stereoisomer.

Targeting a Large Active Site: Structure-Based Design of Nanomolar Inhibitors of Trypanosoma brucei Trypanothione Reductase

Trypanothione reductase (TR) plays a key role in the unique redox metabolism of trypanosomatids, the causative agents of human African trypanosomiasis (HAT), Chagas’ disease, and leishmaniases. Introduction of a new, lean propargylic vector to a known class of TR inhibitors resulted in the strongest reported competitive inhibitor of Trypanosoma (T.) brucei TR, with an inhibition constant Ki of 73 nm, which is fully selective against human glutathione reductase (hGR). The best ligands exhibited in vitro IC50 values (half-maximal inhibitory concentration) against the HAT pathogen, T. brucei rhodesiense, in the mid-nanomolar range, reaching down to 50 nm. X-Ray co-crystal structures confirmed the binding mode of the ligands and revealed the presence of a HEPES buffer molecule in the large active site. Extension of the propargylic vector, guided by structure-based design, to replace the HEPES buffer molecule should give inhibitors with low nanomolar Ki and IC50 values for in vivo studies.

TiO2@UiO-68-CIL: A Metal-Organic-Framework-Based Bifunctional Composite Catalyst for a One-Pot Sequential Asymmetric Morita-Baylis-Hillman Reaction

A chiral ionic liquid (CIL) moiety of a l-pyrrolidin-2-ylimidazole-decorated homochiral UiO-68-type metal-organic framework, UiO-68-CIL (1), was successfully prepared by the combination of a new premodified chiral CIL ligand (H2L-CIL) and ZrCl4 via a solvothermal method. The TiO2-loaded TiO2@UiO-68-CIL (2) was prepared by impregnating 1 in a toluene solution of Ti(OPri)4 and sequential in situ hydrolysis. The obtained 2 can be a bifunctional asymmetric heterogeneous catalyst to successfully promote the one-pot Morita-Baylis-Hillman reaction starting from aromatic alcohols in a tandem way.

PYRIDAZINONES AS PARP7 INHIBITORS

The present invention relates to pyridazinones and related compounds which are inhibitors of PARP7 and are useful in the treatment of cancer.

Pyrrolidine-Oxadiazolone Conjugates as Organocatalysts in Asymmetric Michael Reaction

Pyrrolidine-oxadiazolone based organocatalysts are envisaged, synthesized, and utilized for asymmetric Michael reactions. Results of the investigations suggest that some of the catalysts are indeed efficient for stereoselective 1,4-conjugated Michael additions (dr: >97:3, ee up to 99%) in high chemical yields (up to 97%) often in short reaction time. As an extension, one enantiopure Michael adduct has been utilized to synthesize optically active octahydroindole.

Prolinamides of Aminouracils, Organocatalyst Modifiable by Complementary Modules

We report the synthesis and evaluation of prolinamide organocatalysts that incorporate aminouracils. The features of these catalysts are enhanced NH acidity of the amide because of the electron-withdrawing nature of the heterocycle, an additional hydrogen-bond donor at the α or β positions of this functional group (using 6-aminouracil or 5,6-diaminouracil respectively), and it can be recovered due to its low solubility and used again without decreasing the enantioselectivity. A unique feature of these systems is the self-assembly capability with complementary modules by Watson–Crick interactions. These supramolecular adducts behave differently from the catalyst alone, some of them have lower performance but others improve the selectivity of the product. Therefore, this approach avoids the synthesis of many catalysts.