138228-47-4

Usage

Uses

Used in Organic Synthesis:
(3S,4S)-3,4-BIS[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]PYRROLIDINE is used as a protective group for amines, playing a crucial role in organic synthesis. Its ability to effectively protect amine groups during chemical reactions and synthesis makes it a valuable tool in this field.
Used in Pharmaceutical Development:
(3S,4S)-3,4-BIS[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]PYRROLIDINE is also used as a building block in the development of pharmaceuticals. Its unique structure and silicon-containing moieties provide added stability and functionality, making it a versatile and useful reagent in the creation of new drugs.
Used in Agrochemical Development:
(3S,4S)-3,4-BIS[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]PYRROLIDINE is similarly utilized in the development of agrochemicals, where its protective properties and structural versatility contribute to the synthesis of effective compounds for agricultural applications.

Upstream product

• 136137-86-5 (3R,4R)-3,4-Bis<(tert-butyldimethylsilyl)oxy>-1-benzyl-2,5-pyrrolidinedione 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 138228-45-2 (3S,4S)-1-benzyl-3,4-bis{[(tert-butyl)dimethylsilyl]oxy}pyrrolidine 

Relevant academic research and scientific papers

Copper-catalyzed synthesis of a highly hydroxy-functionalized benzo[e]indolizidine by intramolecular N-arylation

The enantiopure (2S,3S,3aS,5S)-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a] quinoline-2,3,5-triol (2,3,5-trihydroxybenzo[e]indolizidine) framework has been synthesized by a straightforward strategy consisting of 1,3-dipolar cycloaddition of a pyrroline N-oxide to

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.

(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

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.