138228-45-2

Basic information

• Product Name: (3S,4S)-3,4-BIS[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]-1-(PHENYLMETHYL)-PYRROLIDINE
• Synonyms: (3S,4S)-3,4-BIS[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]-1-(PHENYLMETHYL)-PYRROLIDINE
• CAS NO: 138228-45-2
• Molecular Formula: C₂₃H₄₃NO₂Si₂
• Molecular Weight: 421.76
• Mol File: 138228-45-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3S,4S)-3,4-BIS[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]-1-(PHENYLMETHYL)-PYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S)-3,4-BIS[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]-1-(PHENYLMETHYL)-PYRROLIDINE(138228-45-2)
• EPA Substance Registry System: (3S,4S)-3,4-BIS[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]-1-(PHENYLMETHYL)-PYRROLIDINE(138228-45-2)

Safety Data

• Hazardous Substances Data: 138228-45-2(Hazardous Substances Data)

Usage

Uses

Used in Research Applications:
(3S,4S)-3,4-BIS[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]-1-(PHENYLMETHYL)-PYRROLIDINE is used as a chiral reagent and ligand for various metal-catalyzed reactions, facilitating the development of new synthetic methods and improving reaction efficiency.
Used in Organic Synthesis:
(3S,4S)-3,4-BIS[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]-1-(PHENYLMETHYL)-PYRROLIDINE is used as a key intermediate in the preparation of complex natural products and biologically active compounds, enabling the synthesis of novel molecules with potential therapeutic properties.
Used in Enantioselective Synthesis:
(3S,4S)-3,4-BIS[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]-1-(PHENYLMETHYL)-PYRROLIDINE is used as a chiral auxiliary or catalyst in enantioselective synthesis, allowing for the selective formation of enantiomerically pure compounds, which is crucial for the development of enantiomerically pure drugs and agrochemicals.
Used in Asymmetric Catalysis:
(3S,4S)-3,4-BIS[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]-1-(PHENYLMETHYL)-PYRROLIDINE is used as a ligand in asymmetric catalysis, enhancing the enantioselectivity of catalytic reactions and enabling the synthesis of chiral compounds with high enantiomeric excess.
Used in Pharmaceutical Industry:
(3S,4S)-3,4-BIS[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]-1-(PHENYLMETHYL)-PYRROLIDINE is used as a building block or intermediate in the synthesis of pharmaceutical compounds, contributing to the development of new drugs with improved efficacy and selectivity.
Used in Agrochemical Industry:
(3S,4S)-3,4-BIS[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]-1-(PHENYLMETHYL)-PYRROLIDINE is used as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides, with enhanced selectivity and reduced environmental impact.

Upstream product

• 90365-74-5 (3S,4S)-(+)-1-benzyl-3,4-pyrrolidinediol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 100-46-9 benzylamine 
• 75172-31-5 (3R,4R)-1-benzyl-3,4-dihydroxypyrrolidine-2,5-dione 
• 136137-86-5 (3R,4R)-3,4-Bis<(tert-butyldimethylsilyl)oxy>-1-benzyl-2,5-pyrrolidinedione 

Downstream Products

• 138228-47-4 (3S,4S)-3,4-bis<(tert-butyl)dimethylsilyloxy>pyrrolidine 

Relevant articles and documents

(1S,2S,7R,8aS)- and (1S,2S,7S,8aS)-trihydroxyoctahydroindolizine: Two new glycosidase inhibitors by nitrone cycloaddition strategy

The two new epimeric (1S,2S,7R,8aS)- and (1S,2S,7S,8aS)-1,2,7- trihydroxyoctahydroindolizines 4 and 5 have been synthesized via methylenecyclopropane-nitrone cycloaddition-rearrangement methodology employing an enantiomerically pure L-tartaric acid derive

Unexpected rearrangements of rhodium carbenoids containing a pyrrolidin-1-yl group

Ketone- and ester-substituted diazo compounds, which contain a pyrrolidine moiety were treated with dirhodium tetraacetate generating the corresponding rhodium carbenoids. They were expected to insert into a CH bond of the pyrrolidine moiety but reacted differently. The ketone-substituted rhodium carbenoid underwent a Wolff rearrangement. The resulting ketene continued to react by lactamization and electrocyclic ring-opening and gave an acrylamide. The ester-substituted rhodium carbenoid underwent a [1.2]-shift of the (pyrrolidin-1-yl)methyl moiety, which resulted in a methacrylic ester. For each rearrangement a mechanism is suggested.

Low-generation dendrimers with a calixarene core and based on a chiral C2-symmetric pyrrolidine as iminosugar mimics

The preparation of low-generation dendrimers based on a simple calix[4]arene scaffold by insertion of the iminosugar-analogue C 2-symmetric 3, 4-dihydroxypyrrolidine is described. This methodology allows a rapid incorporation of a considerable number of iminosugar-like moieties in a reduced volume and in a well-defined geometry. The inclusion of alkali-metal ions (sodium and potassium) in the polar cavity defined by the acetamide moieties at the lower rim of the calixarene was demonstrated, which allows also the rigidification of the dendrimer structure and the iminosugar presentation in the clusters. The combination of the supra-molecular properties of calixarenes with the advantage of a dendrimeric presentation of repetitive units opens up the possibility of generating well-defined multivalent and multifaceted systems with more complex and/or biologically relevant iminosugars.

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.

Synthesis of (3S,4S)-3,4-dihydroxyprolines from L-tartaric acid

Natural (2S,3S,4S)-3,4-dihydroxyproline (1) and the new (2R,3S,4S)-isomer (7) have been synthesized from L-tartaric acid via cyanosilylation of the cyclic Schiff base.