268224-29-9

Basic information

• Product Name: (R)-1-(tert-butoxycarbonyl)-3,3-dimethyl-1,3-azasilolidine-5-carboxylic acid
• Synonyms: (R)-1-(tert-butoxycarbonyl)-3,3-dimethyl-1,3-azasilolidine-5-carboxylic acid;(5R)-3,3-Dimethyl-1-aza-3-silacyclopentane-1,5-dicarboxylic acid 1-tert-butyl ester;-3,3-dimethyl-1,3-azasilolidine-5-carboxylic acid
• CAS NO: 268224-29-9
• Molecular Formula: C₁₁H₂₁NO₄Si
• Molecular Weight: 259.37424
• Mol File: 268224-29-9.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 358℃
• Flash Point: 171℃
• Appearance: /
• Density: 1.11
• Storage Temp.: 2-8°C
• PKA: 4.22±0.20(Predicted)
• CAS DataBase Reference: (R)-1-(tert-butoxycarbonyl)-3,3-dimethyl-1,3-azasilolidine-5-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-(tert-butoxycarbonyl)-3,3-dimethyl-1,3-azasilolidine-5-carboxylic acid(268224-29-9)
• EPA Substance Registry System: (R)-1-(tert-butoxycarbonyl)-3,3-dimethyl-1,3-azasilolidine-5-carboxylic acid(268224-29-9)

Safety Data

• Hazardous Substances Data: 268224-29-9(Hazardous Substances Data)

Usage

General Description

"(R)-1-(tert-butoxycarbonyl)-3,3-dimethyl-1,3-azasilolidine-5-carboxylic acid" is a chemical compound that belongs to the class of carboxylic acids. It is characterized by the presence of a 1,3-azasilolidine ring and a tert-butoxycarbonyl protecting group. (R)-1-(tert-butoxycarbonyl)-3,3-dimethyl-1,3-azasilolidine-5-carboxylic acid is commonly used in organic synthesis as a building block for the production of various pharmaceuticals and bioactive molecules. Its unique structure and reactivity make it a valuable intermediate in the synthesis of diverse compounds with potential therapeutic applications. Additionally, its chiral nature, due to the presence of the (R)-configuration, makes it particularly useful in asymmetric synthesis for the production of enantiomerically pure compounds.

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

• 1334312-52-5 MK-8325 
• 1334312-50-3 C₄₃H₅₂F₂N₈O₆Si 
• 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 

Relevant articles and documents

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.

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.

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.