13515-74-7

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 1-tritylprolinate is used as a chiral building block for the synthesis of various pharmaceuticals and biologically active molecules. Its ability to provide excellent stereochemical control in asymmetric synthesis makes it a crucial component in the development of drugs for treating depression, anxiety, and other neurological conditions.
Used in Chemical Industry:
In the chemical industry, methyl 1-tritylprolinate serves as an important intermediate due to its unique structural and functional properties. It is utilized in the production of various compounds and materials, contributing to the advancement of chemical research and development.

Upstream product

• 67-56-1 methanol 
• 76-83-5 trityl chloride 
• 147-85-3 L-proline 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 2133-40-6 L-proline methyl ester monohydrochloride 
• 43041-12-9 methyl pyrrolidine-2-carboxylate 

Downstream Products

• 74936-95-1 (S)-α-<(R)-pyrrolidin-2-yl>benzyl alcohol 
• 110529-23-2 (αR,2S)-1-methyl-α-phenyl-2-pyrrolidinemethanol 
• 628292-12-6 (2S)-1-triphenylmethyl-2-pyrrolidinemethanal 
• 628292-15-9 (αR,2S)-α-methyl-1-triphenylmethyl-2-pyrrolidinemethanol 
• 628292-17-1 (αR,2S)-α-ethenyl-1-triphenylmethyl-2-pyrrolidinemethanol 
• 628292-16-0 (αR,2S)-α-(1-methylethyl)-1-triphenylmethyl-2-pyrrolidinemethanol 
• 628292-20-6 (αR,2S)-α-(2-propenyl)-1-triphenylmethyl-2-pyrrolidinemethanol 
• 628292-19-3 (αR,2S)-α-phenyl-1-triphenylmethyl-2-pyrrolidinemethanol 
• 628292-14-8 (αR,2S)-α-(1-butyl)-1-triphenylmethyl-2-pyrrolidinemethanol 
• 1403755-25-8 (S)-2-[(R)-fluoro(phenyl)methyl]pyrrolidine 
• 1403755-26-9 (S)-2-[(S)-fluoro(phenyl)methyl]pyrrolidine 
• 119866-62-5 2-methoxycarbonyl-5-pyrroline 
• 119866-64-7 2-Chloro-3,4-dihydro-2H-pyrrole-2-carboxylic acid methyl ester 
• 119866-63-6 4-Chloro-3,4-dihydro-2H-pyrrole-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Enantioselective ring expansion of prolinol derivatives. Two formal syntheses of (-)-swainsonine

Two enantioselective formal syntheses of (-)-swainsonine have been achieved from l-proline by using an enantioselective ring enlargement of substituted prolinols as the key step. The more efficient synthesis has been achieved in 14 steps with an overall yield of 14%.

NUCLEIC ACID CONJUGATES AND USES THEREOF

Provided herein are conjugates comprising targeting moieties such as sugars, folates and cell-penetrating peptides, which can be used for the improved delivery of agents (e.g., nucleic acids, such as oligonucleotides or mRNAs, or other agents) to cells. The invention provides conjugates and compounds comprising targeting moieties, methods for preparing the same, and intermediates useful in their preparation. In another aspect, the present invention provides formulations (e.g., pharmaceutical compositions) comprising the targetting moiety-containing conjugates and compounds. The present invention also provides methods for delivering agents (e.g., nucleic acids such as oligonucleotides or mRNAs) to a cell, methods for treating and/or preventing a disease or condition in a subject, and methods for modulating gene expression in a cell or a subject. Further, provided herein are kits comprising the conjugates, or formulations thereof; and kits for the preparation of conjugates described herein.

Stereoselective Rearrangement of (Trifluoromethyl)prolinols to Enantioenriched 3-Substituted 2-(Trifluoromethyl)piperidines

3-Substituted 2-(trifluoromethyl)piperidines B were synthesized by ring expansion of (trifluoromethyl)prolinols A, which were obtained from l-proline via an aziridinium intermediate C. The ring opening of the (trifluoromethyl)aziridinium intermediate by different nucleophiles is regio- and diastereoselective.

Fluorinated organocatalysts for the enantioselective epoxidation of enals: Molecular preorganisation by the fluorine-iminium ion Gauche effect

The fluorine-iminium ion gauche effect is triggered upon union of a secondary β-fluoroamine and an α,β-unsaturated aldehyde, providing a useful strategy for controlling the molecular topology of intermediates that are central to organocatalytic processes. The β-fluoroamine (S)-2-(fluorodiphenylmethyl)pyrrolidine (1) is an effective catalyst for the enantioselective epoxidation of α,β-unsaturated aldehydes. A process of structural editing has revealed that the efficiency of this catalyst is due to the (fluorodiphenyl)methyl group when it is embedded in a β-fluoroiminium motif. Epoxidations of challenging cyclic α,β-disubstituted, β,β-disubstituted and α,β,β-trisubstituted enals catalysed by 1 proceed with excellent levels of enantiocontrol (up to 98 % ee). Fluorine finesse. The β-fluoroamine (S)-2-(fluorodiphenylmethyl)pyrrolidine (1) is an effective catalyst for the enantioselective epoxidation of α,β-unsaturated aldehydes (see scheme). Application of this catalyst to challenging cyclic α,β-disubstituted enals, β,β-disubstituted enals, and an α,β,β-trisubstituted enal proceeds in a highly enantioselective fashion (up to 98 % ee). Copyright

Ceric ammonium nitrate-mediated detritylation of tritylated amines

Efficient deprotection of tritylated amines to the corresponding amines mediated by 20 mol % ceric ammonium nitrate [Ce(NH4) 2(NO3)6, CAN], 10 equiv of acetic acid and 15 equiv of water in dichloromethane is presented. This method equally worked well in the case of morpholino nucleosides.

Double chirality transmission in trityl amines: Sensing molecular dynamic stereochemistry by circular dichroism and DFT calculations

Con-figured out: The tert-butyl group can be formally seen as "less" sterically demanding (M) than the methyl group (L). This is the case when a CD-active trityl group at the nitrogen atom is used to report the chirality of the carbon substituent with two

N-Tritylprolinal: An Efficient Building Block for the Stereoselective Synthesis of Proline-Derived Amino Alcohols

N-Tritylprolinal (prepared in four steps from L-proline) shows a very high Felkin diastereoselectivity in its reaction with various nucleophiles, leading to a straightforward and highly stereoselective access to syn-proline-derived amino alcohols.

Polyarylcarbamoylaza- and -carbamoylalkanedioic acids

This invention relates to a class of novel dicarboxy amide derivatives of lipophilic amines which exhibit squalene synthase inhibition properties. More specifically the compounds are bis-aryl and/or heteroaryl alkyl or cycloalkylamino dicarboxy amides. Co