268224-29-9

Usage

Uses

Used in Pharmaceutical Synthesis:
(R)-1-(tert-butoxycarbonyl)-3,3-dimethyl-1,3-azasilolidine-5-carboxylic acid is used as a building block for the production of various pharmaceuticals and bioactive molecules. Its unique structure and reactivity contribute to the synthesis of diverse compounds with potential therapeutic applications.
Used in Asymmetric Synthesis:
In the field of asymmetric synthesis, (R)-1-(tert-butoxycarbonyl)-3,3-dimethyl-1,3-azasilolidine-5-carboxylic acid is utilized as a key intermediate for the production of enantiomerically pure compounds. Its chiral (R)-configuration plays a crucial role in achieving the desired enantioselectivity in the synthesis process.
Used in Organic Synthesis:
(R)-1-(tert-butoxycarbonyl)-3,3-dimethyl-1,3-azasilolidine-5-carboxylic acid is also employed in organic synthesis as a versatile intermediate. Its presence of a 1,3-azasilolidine ring and a tert-butoxycarbonyl protecting group allows for various chemical transformations, enabling the synthesis of a wide range of organic compounds with different functional groups and properties.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 1334313-74-4 (R)-3,3-dimethyl-[1,3]azasilolidine-1,5-dicarboxylic acid 5-[2-(4-bromo-phenyl)-2-oxo-ethyl]ester 1-tert-butyl ester 
• 1334313-65-3 (2R,5R)-2-[(chloromethyl-dimethyl-silanyl)-methyl]-5-isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazine 
• 268224-19-7 (2R,5R)-2-(((iodomethyl)dimethylsilyl)methyl)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine 
• 268224-21-1 (R)-3,3-Dimethyl-[1,3]azasilolidine-5-carboxylic acid methyl ester 
• 268224-27-7 (R)-1-tert-butyl-5-methyl 3,3-dimethyl-1,3-azasilolidine-1,5-dicarboxylate 

Downstream Products

• 1476720-71-4 (R)-5-[4-(4-bromo-phenyl)-1H-imidazol-2-yl]-3,3-dimethyl-[1,3]azasilolidine 
• 1476720-72-5 ((S)-1-{(R)-5-[4-(4-bromo-phenyl)-1H-imidazol-2-yl]-3,3-dimethyl-[1,3]azasilolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester 
• 1476720-73-6 [(S)-1-((R)-3,3-dimethyl-5-{4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-[1,3]azasilolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methylester 
• 1334312-50-3 C₄₃H₅₂F₂N₈O₆Si 
• 1334312-52-5 MK-8325 

Relevant academic research and scientific papers

Discovery of silyl proline containing HCV NS5A inhibitors with pan-genotype activity: SAR development

HCV NS5A inhibitors have shown impressive in vitro potency profiles in HCV replicon assays thus making them attractive components for inclusion in an all oral fixed dose combination treatment regimen. Herein we describe the research efforts that led to the discovery of silyl proline containing HCV NS5A inhibitors such as 7e and 8a with pan-genotype activity profile and acceptable pharmacokinetic properties.

Silaproline helical mimetics selectively form an all-trans PPII helix

The polyproline II helix (PPII) is increasingly recognized as an important element in peptide and protein structures. The discovery of pertinent PPII peptidomimetics is of great interest to tune physical properties of the targeted structure. A series of silaproline oligomers from dimer to pentamer were synthesized. CD studies, NMR spectroscopy and molecular modeling revealed that the ribbon preferentially populates the polyproline type II secondary structure in both [D]chloroform and [D4]MeOH. The characteristics of this new lipophilic PPII-like helix were determined.

COMPOUNDS FOR THE TREATMENT OF MEDICAL DISORDERS

Compounds, methods of use, and processes for making inhibitors of complement Factor D comprising Formula (I), or a pharmaceutically acceptable salt or composition thereof The inhibitors described herein target Factor D and inhibit or regulate the complement cascade. The inhibitors of Factor D described herein reduce the excessive activation of complement.

ARYL, HETEROARYL, AND HETEROCYCLIC COMPOUNDS FOR TREATMENT OF MEDICAL DISORDERS

Compounds, methods of use, and processes for making inhibitors of complement Factor D comprising Formula I, or a pharmaceutically acceptable salt or composition thereof wherein R12 or R13 on the A group is an aryl, heteroaryl or heterocycle (R32) are provided. The inhibitors of Factor D described herein reduce the excessive activation of complement.

Asymmetric Synthesis of N-Boc-(R)-Silaproline via Rh-Catalyzed Intramolecular Hydrosilylation of Dehydroalanine and Continuous Flow N-Alkylation

An asymmetric synthesis of a silicon-containing proline surrogate, N-Boc-(R)-silaproline (1), is described. Starting from N-Boc-dehydroalanine ester, deprotonation, followed by N-alkylation with chloromethyldimethylsilane under flow conditions, afforded the N-alkylated product 8 in 91% yield. An unprecedented enantioselective (NBD)2RhBF4/Josiphos 404-1 catalyzed 5-endo-trig hydrosilylation afforded the silaproline ester in 85-90% yield and >95% ee. Subsequent saponification and salt formation upgraded 1 to >99% ee.

FUSED TRICYCLIC SILYL COMPOUNDS AND METHODS OF USE THEREOF FOR THE TREATMENT OF VIRAL DISEASES

no abstract published

IAP ANTAGONISTS

There are disclosed compounds that modulate the activity of inhibitors of apoptosis (lAPs), pharmaceutical compositions containing said compounds and methods of treating proliferative disorders and disorders of dysregulated apoptosis, such as cancer, utilizing the compounds of the invention.

HEPATITIS C VIRUS INHIBITORS

The invention provides compounds of formulas (I) or (II): wherein the variables are defined in the specification, or a pharmaceutically-acceptable salt thereof, that are inhibitors of replication of the hepatitis C virus. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat hepatitis C viral infections, and processes and intermediates useful for preparing such compounds.

SILYL-CONTAINING HETEROCYCLIC COMPOUNDS AND METHODS OF USE THEREOF FOR THE TREATMENT OF VIRAL DISEASES

The present invention relates to novel Silyl-Containing Heterocyclic Compounds of Formula (I): and pharmaceutically acceptable salts thereof, wherein A, B, C, D, E, F and L are as defined herein. The present invention also relates to compositions comprising at least one Silyl-Containing Heterocyclic Compound, and methods of using the Silyl-Containing Heterocyclic Compounds for treating or preventing HCV infection in a patient.

SILYL-CONTAINING HETEROCYCLIC COMPOUNDS AND METHODS OF USE THEREOF FOR THE TREATMENT OF VIRAL DISEASES

The present invention relates to novel Silyl-Containing Heterocyclic Compounds of Formula (I): (I) and pharmaceutically acceptable salts thereof, wherein A, B, C, D and R2 are as defined herein. The present invention also relates to compositions comprising at least one Silyl-Containing Heterocyclic Compound, and methods of using the Silyl-Containing Heterocyclic Compounds for treating or preventing HCV infection in a patient.