540501-56-2

Usage

Uses

Used in Pharmaceutical Production:
1-Boc-2-hydroxyMethyl-4-M... is used as an intermediate compound for the synthesis of various pharmaceuticals. Its protective Boc group and alcohol functionality make it a valuable building block in the development of new drugs.
Used in Biochemical Research:
1-Boc-2-hydroxyMethyl-4-M... is used as a reagent in biochemical research, where its protective group and alcohol functionality can be exploited to study the interactions of biomolecules and their potential applications in medicine.
Used in Organic Synthesis:
1-Boc-2-hydroxyMethyl-4-M... is used as a key component in the synthesis of other organic compounds, where its protective Boc group and alcohol functionality can be strategically removed or modified to yield desired products. This versatility makes it a valuable asset in the field of organic chemistry.

Upstream product

• 1560646-40-3 C₁₁H₁₉NO₃ 
• 364750-81-2 N-tert-Butyloxycarbonyl-(2S,4S)-4-methylproline 
• 540501-65-3 (S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenylthio)methylenepyrrolidine 
• 220993-22-6 (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-oxopyrrolidine-1-carboxylate 
• 51-35-4 4R-4-hydroxyproline 
• 125653-58-9 (2S,4R)-2-(tert-butyldimethylsilanyloxymethyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 61478-26-0 tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 1560643-76-6 C₄₃H₅₄N₆O₄ 
• 1560639-00-0 C₄₇H₆₀N₈O₆ 
• 1283145-91-4 ((2S,4S)-1-(4-bromophenyl)-4-methylpyrrolidin-2-yl)methanol 
• 1283145-92-5 2-((2S,4S)-1-(4-bromophenyl)-4-methylpyrrolidin-2-yl)acetonitrile 
• 1283145-93-6 2-((2S,4S)-4-methyl-1-(4-(2-methylbenzyl)phenyl)pyrrolidin-2-yl)acetonitrile 
• 1283142-47-1 2-((2S,4S)-4-methyl-1-(4-(2-methylbenzyl)phenyl)pyrrolidin-2-yl)acetic acid trifluoroacetic acid salt 
• 901139-63-7 N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S,4S)-4-methylprolyl-glycine benzyl ester 
• 901139-37-5 N-9-fuorenylmethoxycarbonyl-(2S)-prolyl-(2S,4S)-4-methylprolyl-glycine benzyl ester 
• 901139-29-5 N-tert-butyloxycarbonyl-(2S,4S)-4-methylprolyl-glycine benzyl ester 
• 364750-81-2 N-tert-Butyloxycarbonyl-(2S,4S)-4-methylproline 

Relevant academic research and scientific papers

Asymmetric hydrogenations for the synthesis of boc-protected 4-alkylprolinols and prolines

The utility of 4-substituted prolinols and their corresponding prolines in peptides, peptidomimetics, and natural products has motivated researchers to find new and efficient routes for their preparation. Herein, we report a general approach to the synthesis of Boc-protected 4-alkylprolinols and prolines via a divergent asymmetric hydrogenation strategy. Intermediate exocyclic olefins were prepared by Wittig-type reactions with ketone 6 and subjected to hydroxyl and sterically directed reductions. The Crabtree catalyst (Ir[COD] PyPCy3PF6) proved to be highly effective in diastereoselective hydrogenations to give trans- substituted pyrrolidines (9). Good facial selectivities were also observed in heterogeneous hydrogenations with Raney-nickel to obtain cis-substituted pyrrolidines (11). Employing this strategy, we describe the synthesis of novel prolinol and proline-based building blocks for incorporation into biologically relevant peptidomimetics.

Stereodivergent and stereoselective synthesis of cis-and trans-4-substituted prolinols

- Stereoselective synthesis of 4-substituted prolinol derivatives has been developed. Thus, Suzuki-Miyaura cross-coupling of vinyl tritiate provided the common synthetic intermediates toward the stereodivergent synthesis of cis- and ira?s-4-substituted prolinols. These two kinds of target compounds were obtained by diastereoselective hydrogenation of the coupling products with Pd/C and Crabtree catalyst, respectively. In addition, the obtained 4-substituted prolinol was transformed to the corresponding proline derivative via oxidation in one step.

Discovery of Pyrrolidine-Containing GPR40 Agonists: Stereochemistry Effects a Change in Binding Mode

A novel series of pyrrolidine-containing GPR40 agonists is described as a potential treatment for type 2 diabetes. The initial pyrrolidine hit was modified by moving the position of the carboxylic acid, a key pharmacophore for GPR40. Addition of a 4-cis-CF3 to the pyrrolidine improves the human GPR40 binding Ki and agonist efficacy. After further optimization, the discovery of a minor enantiomeric impurity with agonist activity led to the finding that enantiomers (R,R)-68 and (S,S)-68 have differential effects on the radioligand used for the binding assay, with (R,R)-68 potentiating the radioligand and (S,S)-68 displacing the radioligand. Compound (R,R)-68 activates both Gq-coupled intracellular Ca2+ flux and Gs-coupled cAMP accumulation. This signaling bias results in a dual mechanism of action for compound (R,R)-68, demonstrating glucose-dependent insulin and GLP-1 secretion in vitro. In vivo, compound (R,R)-68 significantly lowers plasma glucose levels in mice during an oral glucose challenge, encouraging further development of the series.

As hepatitis c inhibitor spiro compound and its use in medicine

The invention provides a spiro compound serving as a hepatitis c inhibitor and application thereof in a medicine. The compound is a compound as shown in a formula (I) or a stereisomer, a geometric isomer, a tautomer, nitric oxide, an aquo-complex, a solvate, a metabolite, pharmaceutically acceptable salt or prodrug of the compound as shown in the formula (I). The invention also provides a pharmaceutical composition containing the compound, application of the compound and the pharmaceutical composition in inhibition of HCV (Hepatitis C Virus) copy and HCV virus protein, as well as the application of the compound and the pharmaceutical composition in prevention, handling, treatment or relieving of HCV infection or hepatitis c disease for a patient. The formula I is as shown in the specification.

Bridged Ring compounds As Hepatitis C Virus (HCV) Inhibitors And Pharmaceutical Applications Thereof

Provided herein is a compound having Formula (I), or a stereoisomer, a geometric isomer, a tautomer, an N-oxide, a hydrate, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof, which can be used for treating HCV infection or a HCV disorder. Also provided herein are pharmaceutical compositions comprising the compounds disclosed herein, which can be used for treating HCV infection or a HCV disorder.

BRIDGED RING COMPOUNDS AS HEPATITIS C VIRUS (HCV) INHIBITORS AND PHARMACEUTICAL APPLICATIONS THEREOF

Provided herein is a compound having Formula (I), or a stereoisomer, a geometric isomer, a tautomer, an N-oxide, a hydrate, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof, which can be used for treating HCV infection or a HCV disorder. Also provided herein are pharmaceutical compositions comprising the compounds disclosed herein, which can be used for treating HCV infection or a HCV disorder.

BRIDGED RING COMPOUNDS AS HEPATITIS C VIRUS INHIBITORS, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF

Provided herein is a compound of formula (I) or a stereoisomer, a geometric isomer, a tautomer, an N-oxide, a hydrate, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof, which can be used for treating HCV infection or a HCV disorder. Also provided herein are a pharmaceutical composition comprising the compound and the use of the compound and the pharmaceutical composition thereof, which can also be used for treating HCV infection or a HCV disorder.

PYRROLIDINE GPR40 MODULATORS

The present invention provides compounds of Formula (I): or a stereoisomer, or a pharmaceutically acceptable salt thereof, wherein all of the variables are as defined herein. These compounds are GPR40 G protein-coupled receptor modulators which may be used as medicaments.

Collagen mimics

Novel collagen mimics are disclosed with a tripeptide unit having the formula (Xaa-Yaa-Gly)n, where one of the positions Xaa or Yaa is a bulky, non-electron withdrawing proline derivative. By substituting a proline derivative at either the Xaa or Yaa position in the native collagen helix, the stability of the helix is increased due solely to steric effects relative to prior known collagen-related triple helices. Methods are also disclosed for making the novel collagen mimics.

Reciprocity of steric and stereoelectronic effects in the collagen triple helix

In previous work, we demonstrated that 4-fluoroproline residues can contribute greatly to the conformational stability of the collagen triple helix, and that this stability arises from stereoelectronic effects that fix the pucker of the pyrrolidine ring and thereby preorganize the backbone properly for triple-helix formation. Here, we take a reciprocal approach, demonstrating that the steric effect of a 4-methyl group confers stability similar to that from a 4-fluoro group in the opposite configuration. Such fundamental interplay between steric and stereoelectronic effects is heretofore unknown in proteinsnatural or syntheticand provides a new means to modulate conformational stability. Copyright