134756-75-5

Usage

Uses

Used in Organic Synthesis:
(2S)-2-([(tert-butyl)(dimethyl)silyl]oxymethyl)pyrrolidine is used as a protecting group for amines during organic synthesis. Its ability to be easily removed under mild conditions allows chemists to protect amine functional groups from unwanted reactions, facilitating the synthesis of complex molecules.
Used in Chemical Research and Development:
In the field of chemical research and development, (2S)-2-([(tert-butyl)(dimethyl)silyl]oxymethyl)pyrrolidine serves as an important tool for the creation of complex molecules. Its versatility and the ease with which the tert-butyl and dimethylsilyl groups can be removed make it a preferred choice for protecting sensitive functional groups in the synthesis of intricate chemical structures.

Upstream product

• 128359-99-9 (2S)-1-(Benzyloxycarbonyl)-2-<<(tert-butyldimethylsilyl)oxy>methyl>pyrrolidine 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 147-85-3 L-proline 
• 199117-77-6 (S)-2-(hydroxymethyl)-1-(pyridin-2-yl)pyrrolidine 

Downstream Products

• 862107-71-9 (2S)-(tert-butyldimethylsilanyloxymethyl)-1-[(1R)-1-(tert-butyldiphenylsilanyloxymethyl)-4-methoxymethoxy-2-butynyl]pyrrolidine 
• 1416046-10-0 2-[ (2S)-2-{[bis(2-methylphenyl)phosphanyl]methyl}pyrrolidin-1-yl]-1,3-benzoxazole 
• 1416046-11-1 2-[(2S)-2-{[bis(2-methylphenyl)phosphanyl]methyl}pyrrolidin-1-yl]-1,3-benzothiazole 
• 1416046-17-7 2-{(2S)-2-[(dicyclohexylphosphanyl)methyl]pyrrolidin-1-yl}-1,3-benzoxazole 
• 1416046-19-9 2-{(2S)-2-[(dicyclohexylphosphanyl)methyl]pyrrolidin-1-yl}-1,3-benzothiazole 
• 1613376-99-0 C₂₃H₃₄N₂O₄SSi 
• 1613377-21-1 C₂₃H₂₇N₅O₆S 
• 1613377-11-9 C₂₃H₂₉N₅O₆S 
• 1613377-19-7 C₂₄H₃₀N₄O₆S₂ 
• 204580-50-7 2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidine-1-carboxylic acid 4-(7-isopropoxy-5,6-dimethoxy-4-oxo-4H-chromen-2-ylsulfanyl)-phenyl ester 
• 862107-66-2 (2S,3R,4E)-2-benzyloxy-1-[(2S)-2-(tert-butyldimethylsilanyloxymethyl)pyrrolidin-1-yl]-6-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxymethyl-4-hexenone 
• 862107-72-0 (2S)-(tert-butyldimethylsilanyloxymethyl)-1-[(1R)-1-(tert-butyldiphenylsilanyloxymethyl)-4-methoxymethoxy-2-butenyl]pyrrolidine 

Relevant academic research and scientific papers

FUSED RING COMPOUNDS

This invention pertains to fused ring compounds of Formula (I), as further detailed herein, which are used for the inhibition of Ras proteins, as well as compositions comprising these compounds and methods of treatment by their administration.

Asymmetric Synthesis of α-Aminoboronates via Rhodium-Catalyzed Enantioselective C(sp3)-H Borylation

α-Aminoboronic acids, isostructural boron analogues of α-amino acids, have received much attention because of the important biomedical applications implicated for compounds containing this structure. Additionally, the inherent versatility of α-aminoboronic acids as synthetic intermediates through diverse carbon-boron bond transformations makes the efficient synthesis of these compounds highly desirable. Here, we present a Rh-monophosphite chiral catalytic system that enables a highly efficient enantioselective borylation of N-adjacent C(sp3)-H bonds for a range of substrate classes including 2-(N-alkylamino)heteroaryls and N-alkanoyl- or aroyl-based secondary or tertiary amides, some of which are pharmaceutical agents or related compounds. Various stereospecific transformations of the enantioenriched α-aminoboronates, including Suzuki-Miyaura coupling with aryl halides and the Rh-catalyzed reaction with an isocyanate derivative of α-amino acid, affording a new peptide chain elongation method, have been demonstrated. As a highlight of this work, the borylation protocol was successfully applied to the catalyst-controlled site-selective and stereoselective C(sp3)-H borylation of an unprotected dipeptidic compound, allowing remarkably streamlined synthesis of the anti-cancer drug molecule bortezomib and offering a straightforward route for the synthesis of privileged molecular architectures.

Transition Metal-Free Selective Double sp3 C-H Oxidation of Cyclic Amines to 3-Alkoxyamine Lactams

The first chemical method for selective dual sp3 C-H functionalization at the alpha-and beta positions of cyclic amines to their corresponding 3-alkoxyamine lactams is reported. Unlike traditional Cα-H oxidation of amines to amides mediated by transition metals, the present protocol, which involves the use of NaClO2/TEMPO/NaClO in either aqueous or organic solvent, not only allows the Cα-H oxidation but also the subsequent functionalization of the unreactive β-methylene group in an unprecedented tandem fashion and using environmentally friendly reactants.

Low-valent titanium-catalyzed deprotection of allyl- and propargyl-carbamates to amines

In the presence of Me3SiCl, Ti(O-i-Pr)4/Mg and CpTiCl3/Mg reagents effectively catalyzed the deprotection of allyloxycarbonyl (alloc)- and propargyloxycarbonyl (poc)-protected amines in THF at around room temperature to produce parent amines in good yields. Alloc- and poc-protected secondary amines were smoothly deprotected to parent amines by a reaction catalyzed by a Ti(O-i-Pr)4/Me3SiCl/Mg reagent. The deprotection of alloc- and poc-protected primary amines was successfully catalyzed by a CpTiCl3/Me3SiCl/Mg reagent.

DIHYDROQUINOLINE-2-ONE DERIVATIVES

The invention provides novel compounds having the general formula (I) wherein R1, R2, R3, R4, R5, R6, R7, A1, A2 and A3 are as described herein, compositions including the compounds and methods of using the compounds. These compounds are useful for therapy or prophylaxis in a mammal, and in particular as aldosterone synthase (CYP11B2 or CYP11B1) inhibitors for the treatment or prophylaxis of chronic kidney disease, congestive heart failure, hypertension, primary aldosteronism and Cushing syndrome.

NEW DIHYDROQUINOLINE-2-ONE DERIVATIVES

The invention provides novel compounds having the general formula (I) wherein R1, R2, R3, R4? R5, R6, R7, A1, A2 and A3 are as described herein, compositions including the compounds and methods of using the compounds.

NEW BICYCLIC DIHYDROISOQUINOLINE-1-ONE DERIVATIVES

The invention provides novel compounds having the general formula (I) wherein R1, R2, R3, R4? R5, R6, A1, A2, A3, A4, A5 and n are as described herein,compositions including the compounds and methods of using the compounds as aldosterone synthase (CYP11B2 or CYP11B1) inhibitors for the treatment or prophylaxis of chronic kidney disease, congestive heart failure, hypertension, primary aldosteronism and Cushing syndrom.

NEW BICYCLIC DIHYDROISOQUINOLINE-1-ONE DERIVATIVES

The invention provides novel compounds having the general formula (I) wherein R1, R2, R3, R4, R5, R6, A1, A2, A3, A4, A5 and n are as

Prolinol tert-butyldiphenylsilyl ether as organocatalyst for the asymmetric michael addition of cyclohexanone to nitroolefins

The direct Michael additions of cyclohexanone to nitroolefins catalyzed by prolinol tert-butyldiphenylsilyl ether were conducted successfully in good yields (up to 99%) and high stereo-selectivities (up to 98:2 diastereomeric ratio and 95% enantiomeric ex

Synthesis and evaluation of carbamate prodrugs of a phenolic compound

A series of carbamates of the phenolic compound 1 were prepared and evaluated in vivo as its prodrug. Each carbamate was orally administered to rats, and plasma concentrations of the parent compound 1 were measured with the passage of time. We judged which carbamate was suitable for the prodrug of 1 from both the AUC value of 1 and absence of the carbamate in plasma. The AUC value of 1 after oral administration of 2b was approximately 40-fold higher than that for an administration of 1, and the bioconversion from 2b to 1 was excellent. As a whole, di-substituted carbamates resulted in higher plasma concentrations of 1 than did mono-substituted ones. However di-substituted carbamates were almost always detected in plasma. As a result, we found that the ethycarbamoyl derivative 2b demonstrates the best prodrug property in this series.