74936-95-1

Usage

Uses

Used in Pharmaceutical Industry:
(S)-α-<(R)-pyrrolidin-2-yl>benzyl alcohol is used as a chiral auxiliary for the synthesis of chiral α-amino acids and other pharmacologically important molecules. Its ability to control the stereochemistry of chemical reactions is crucial in producing these complex molecules with the desired chirality, which is essential for their biological activity and therapeutic effects.
Used in Organic Synthesis:
In the field of organic synthesis, (S)-α-<(R)-pyrrolidin-2-yl>benzyl alcohol serves as a valuable tool for asymmetric synthesis. Its unique structure allows chemists to achieve a higher level of selectivity and enantiomeric purity in the synthesis of chiral compounds, which is vital for the development of more effective and safer drugs.
Used in Fine Chemicals Production:
(S)-α-<(R)-pyrrolidin-2-yl>benzyl alcohol is also utilized in the production of fine chemicals, where its chiral properties are harnessed to create high-quality specialty chemicals with specific applications in various industries, including fragrances, flavors, and agrochemicals.

Upstream product

• 591-51-5 phenyllithium 
• 74936-94-0 (S)-(-)-5-benzoyl-2-pyrrolidinone 
• 100-58-3 phenylmagnesium bromide 
• 106202-17-9 ethyl (S)-2-benzoylpyrrolidine-1-carboxylate 
• 147-85-3 L-proline 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 1266251-94-8 (1R,2S)-2-(hydroxyphenylmethyl)pyrrolidine-1-carboxylic acid tert-butyl ester 
• 69610-41-9 Boc-L-Pro-H 
• 55456-48-9 ((2S)-1-p-toluenesulfonyl-2-pyrrolidinyl)methanol 
• 67488-65-7 (S)-methyl 1-tosylpyrrolidine-2-carboxylate 
• 101250-69-5 (S)-1-<(4-methylphenyl)sulfonyl>-2-pyrrolidinecarboxaldehyde 
• 5700-74-3 (S)-N-(ethoxycarbonyl)proline 
• 4931-66-2 methyl (S)-pyroglutamate 
• 179918-60-6 (2S)-1-triphenylmethyl-2-pyrrolidinemethanol 

Downstream Products

• 110529-23-2 (αR,2S)-1-methyl-α-phenyl-2-pyrrolidinemethanol 
• 1403755-26-9 (S)-2-[(S)-fluoro(phenyl)methyl]pyrrolidine 
• 220058-21-9 (R)-1-[(2S)-1-benzylpyrrolidin-2-yl](phenyl)methanol 
• 250589-64-1 (2S,3S)-1-benzyl-3-hydroxy-2-phenylpiperidin 
• 866219-00-3 (4R,5S)-oxazaphospholidine 
• 866219-07-0 2-chloro-1,3,2-oxazaphospholidine 

Relevant academic research and scientific papers

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.

Highly stereoselective syntheses of proline-derived vicinal amino alcohols through grignard addition onto N-tosylprolinal

A highly diastereoselective Grignard addition to N-tosyl-l-prolinal has been developed to deliver a variety of proline-derived vicinal amino alcohols in good to excellent yields with high diastereoselectivities. A similar selectivity was also obtained by using N-tosyl-d-prolinal. The methodology has been applied to the synthesis of medicinally important 3-hydroxy-2-phenylpiperidines.

Mass Spectrometric Screening of Racemic Amine Catalysts for Enantioselective Michael Additions

In extension of a concept of Lloyd-Jones, based on the combination of a racemic catalyst with a scalemic substrate, we have recently developed a method for determining the enantioselectivity of a chiral catalyst from its racemic form by mass spectrometric screening of a non-equal mixture of two mass-labeled quasi-enantiomeric substrates. After an initial proof of principle using palladium-catalyzed allylic substitution as test reaction, we report now the successful application of this approach to the screening of chiral amines as catalysts for the enantioselective Michael addition to α,β-unsaturated aldehydes. The results confirm that our method allows fast and reliable evaluation of chiral racemic catalysts. This opens up new possibilities for investigating catalyst structures that are not easily available in enantiomerically pure form.

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

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.

Enantioselective synthesis of 2,3-disubstituted piperidines from (S)- methylpyroglutamate

N-methoxy-N-methylamide derived from (S)-methylpyroglutamate was prepared in good yield and allowed the addition of Grignard reagents. Erythro (2S)-1-benzyl-2-hydroxybenzyl pyrrolidine obtained by this way was converted into (2S,3R)-1-benzyl-3-hydroxy-2-phenylpiperidine and its chloro analog.

Asymmetric Synthesis of Optically Active threo- and erythro-Pyrrolidinylbenzyl Alcohol by the Highly Stereospecific Arylation of (S)-Proline and the Subsequent Highly Diastereoselective Reduction of the α-Amino Ketone

Optically active α-amino phenyl ketones in 92-94percent enantiomeric excess (e.e.) were obtained from the stereospecific arylation of (S)-proline or its derivatives by Friedel-Crafts reaction of by Grignard reaction.The subsequent complementary diastereoselective reductions of the α-amino ketone afforded respectively (S)- and (R)-α-benzyl alcohol in 93-100percent e.e. and in 100percent diastereoisomeric excess.The stereochemical course of the reduction of the α-amino ketone is discussed.

Catalytic Asymmetric Induction. Highly Enantioselective Addition of Dialkylzincs to Aldehydes Using Chiral Pyrrolidinylmethanols and Their Metal Salts

A series of chiral pyrrolidinylmethanols were synthesized from (S)-proline.Optically active secondary alcohols (R and S enantiomers, respectively) in up to 100percent enantiomeric excess (ee) were obtained in high yields from the enantioselective addition of dialkylzincs to aldehydes catalyzed by 2-5 mol percent of chiral pyrrolidinylmethanols.The sense of the asymmetric induction and the degrees of enantioselectivities were highly dependent on the structure of the catalysts. (+)-DPMPM (3, tertiary amino tertiary alcohol) catalyzed the reaction of aryl, α,β-unsaturated, and aliphatic aldehydes to afford (S) alcohols in high ee's.When the lithium salt of 3 was employed as catalyst in the reactions of aryl and α,β-unsaturated aldehydes, the ee's of (S) alcohols reached 100percent.On the other hand, (-)-erythro-PNPM (10, tertiary amino secondary alcohol) afforded (R) alcohols in high ee (100percent ee).The steric course of the reaction is discussed.

Highly Stereospecific Arylation Of (S)-Proline and Complementary Highly Diastereoselective Reduction of the α-Amino Ketone. Asymmetric Synthesis of (1S,2'S)- and (1R,2'S)-Phenyl(2'-pyrrolidinyl)methanol

Both optically active threo- and erythro-phenyl(2'-pyrrolidinyl)methanol (93-100percent enantiomeric excess, 100percent diastereoisomeric excess) were synthesised from (S)-proline by a stereospecific arylation and the subsequent complementary diastereoselective reduction of the α-amino ketone.