201601-50-5

Usage

Uses

Used in Organic Synthesis:
(3S,4S)-1-benzyl-3-(tert-butyldimethylsilyl)oxy-4-hydroxypyrrolidine is used as a key intermediate for the synthesis of complex organic molecules. Its unique structure and functional groups facilitate the creation of a wide range of compounds with diverse applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (3S,4S)-1-benzyl-3-(tert-butyldimethylsilyl)oxy-4-hydroxypyrrolidine is used as a building block for the development of new pharmaceuticals. Its structural features make it a valuable component in the design and synthesis of biologically active molecules with potential therapeutic properties.
Used in Pharmaceutical Development:
(3S,4S)-1-benzyl-3-(tert-butyldimethylsilyl)oxy-4-hydroxypyrrolidine is utilized as a starting material in the pharmaceutical industry for the creation of novel drugs. Its versatility in organic synthesis and compatibility with various chemical reactions make it an attractive candidate for the development of innovative medications.
Used in the Synthesis of Biologically Active Molecules:
(3S,4S)-1-benzyl-3-(tert-butyldimethylsilyl)oxy-4-hydroxypyrrolidine is employed as a synthetic precursor for the production of biologically active molecules. Its unique structural elements and functional groups enable the creation of molecules with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 90365-74-5 (3S,4S)-(+)-1-benzyl-3,4-pyrrolidinediol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 75172-31-5 (3R,4R)-1-benzyl-3,4-dihydroxypyrrolidine-2,5-dione 
• 100-46-9 benzylamine 

Downstream Products

• 201601-51-6 Succinic acid mono-[(3S,4S)-1-benzyl-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-3-yl] ester 
• 952708-30-4 (3R,4S)-1-benzyl-3-amino-4-(tert-butyldimethylsilyloxy)pyrrolidine 
• 267234-16-2 (3R,4S)-1-benzyl-3-(tert-butoxycarbonylamino)-4-(tert-butyldimethyl-silyloxy)pyrrolidine 
• 1260593-44-9 C₁₈H₂₆N₂O₄ 
• 952709-09-0 tert-butyl (3R,4S)-4-(tert-butyldimethylsilyloxy)-1-((2S)-2-(1-(6-fluoro-3'-methylbiphenyl-2-yl)-5-methoxypentyl)morpholine-4-carbonyl)pyrrolidin-3-ylcarbamate 
• 267234-14-0 (3R,4S)-3-azido-1-benzyl-4-(tert-butyldimethylsilyloxy)pyrrolidine 

Relevant academic research and scientific papers

Electrostatics Favor PNA : DNA Stability over Stereochemistry in Pyrrolidine-Based Cationic Dual-Backbone PNA Analogues

Modifications to the peptide nucleic acid (PNA) backbone has been well known to alter the thermodynamical parameters of PNA : DNA complexes to broaden their utility for different applications. Electrostatic interactions between a modified PNA having a positively charged backbone and the negatively charged DNA has been shown to enhance thermal stabilities of PNA : DNA complexes at various instances. On the other hand, chiral introduction in PNA backbone leads to stereochemical preference that affects binding properties. However, the interplay between electrostatics and stereochemistry has not been systematically studied so far. Herein, we report the synthesis and biophysical characterization of cationic PNA named dapPNA, first of its kind, having a dual PNA backbone constituting of a pyrrolidine ring having a β-substitution. One of the aims of this study was to investigate the role of electrostatics over stereochemical preferences. The results show that electrostatic attraction between cationic dapPNA and negatively charged DNA overcomes the unfavorable stereochemical effects and enhances stability of PNA : DNA complexes. Moreover, two different PNA backbones derived from a single PNA monomer expands the repertoire of pyrrolidine based PNA analogues.

Pyrrolidine-based cationic γ-peptide: a DNA-binding molecule works as a potent anti-gene agent

Pyrrolidine-based cationic peptides showing high stability to enzyme degradation and strong binding affinity towards DNA are widely investigated as tools to interfere in gene expression. Several studies have been focused on γ-peptide analogs with modifications on the peptide backbone in the attempt to overcome solubility, uptake, and aggregation issues. Pyrrolidine-based γ-peptide derivatives having two different modes of backbone conformation show interesting properties in terms of secondary structure and affinity of binding towards nucleic acids. In this paper, we illustrate our results obtained on two cationic 8-mer γ-peptides Gp1 and Gp2, and how they differ in side-chain spacing along the backbone was tested for DNA binding and DNA transfection activity. Both γ-peptides are stable toward protease digestion. Gp1 binds to DNA more tightly than GP2. This binding ability of Gp1 is attributed to its characteristic of single-chain PPII-like conformation. The Gp1 shows a reduction in its electrophoretic mobility when treated with plasmid DNA. The DNA transfection ability of γ-peptide Gp1 was compared with commercially available transfection reagent Effectene. In each case, Gp1 significantly enhanced the transfection efficiency (40%) of plasmid in Schneider cells compared to the commercial reagent (18%). The other γ-peptide GP2 is not active. [Figure not available: see fulltext.]

Enantiospecific Synthesis of (3 R,4 R)-1-Benzyl-4-fluoropyrrolidin-3-amine Utilizing a Burgess-Type Transformation

Manufacture of an EGFR inhibitor required the asymmetric synthesis of a key 3,4-trans-substituted pyrrolidine suitable for pilot-plant scale. The initial synthetic route utilized reagents and intermediates that posed safety concerns due to their energetic potential and then required supercritical fluid chromatography to access the desired single enantiomer. Burgess-type reagents provide tremendous utility in organic synthesis but see limited use on large scales because of their high cost and instability. Nevertheless, extensive process development led to a scale-friendly process where in situ formation of a Boc-Burgess reagent enabled access to a chiral cyclic sulfamate from inexpensive materials. ReactIR monitoring was used to study intermediate stability and enabled processing on a multikilogram scale. The sulfamate was converted to trans-3-fluoro-4-aminopyrrolidine 1 with complete stereospecificity. Intermediate crystallinity offered purity control points where byproducts and impurities were rejected, avoiding the need for chromatography.

RENIN INHIBITORS

Disclosed are compounds according to Formula (I): wherein the variables are defined herein. Such compounds are can bind aspartic proteases to inhibit their activity. They are useful in the treatment or amelioration of diseases associated with aspartic pro

Efficient stereospecific synthesis of (S,S)-3-methoxy-4-methylaminopyrrolidine

Efficient stereospecific synthesis of (S,S)-3-methoxy-4-methylaminopyrrolidine, an important intermediate for a novel quinolone antitumor agent AG-7352 is presented. Starting from either D- or L-tartaric acid, a stereospecific synthesis of the chiral pyrrolidine was achieved via two SN2 displacement reactions. From the results of this synthetic study, the absolute structure of AG-7352 was chemically determined.

Synthesis of enantiopure protected 3-hydroxy-4-amino pyrroline N-oxides

The synthesis of new five-membered enantiopure cyclic nitrones bearing protected cis vicinal amino and hydroxy functionalities is reported. The key step was a Mitsunobu reaction, which allowed placement of an azido group, with inversion of configuration, at the reacting centre. Cycloaddition of the novel nitrones to but-3-en-1-ol followed by simple elaboration of the adducts readily afforded protected amino dihydroxy indolizidines. (C) 2000 Elsevier Science Ltd.

New enantiomerically pure oligomeric macrocycles based on a 3,4-dihydroxypyrrolidine nucleus

(3S,4S)-N-Benzyl-3,4-dihydroxypyrrolidine 1 has been used as a building block for new enantiopure macrocyclic polyesters. Two different synthetic approaches are presented leading to complementary results. The structure of the macrocycles synthesized has been confirmed by NMR spectroscopy and FAB mass spectrometry, and that for dimer 8 has been confirmed by X-ray analysis.