401564-17-8

Basic information

• Product Name: 1,2-Pyrrolidinedicarboxylic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, 1-(1,1-dimethylethyl) ester, (2S,4S)-
• CAS NO: 401564-17-8
• Molecular Formula: C16H31NO5Si
• Molecular Weight: 345.511
• Mol File: 401564-17-8.mol

Chemical Properties

• CAS DataBase Reference: 1,2-Pyrrolidinedicarboxylic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, 1-(1,1-dimethylethyl) ester, (2S,4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Pyrrolidinedicarboxylic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, 1-(1,1-dimethylethyl) ester, (2S,4S)-(401564-17-8)
• EPA Substance Registry System: 1,2-Pyrrolidinedicarboxylic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, 1-(1,1-dimethylethyl) ester, (2S,4S)-(401564-17-8)

Safety Data

• Hazardous Substances Data: 401564-17-8(Hazardous Substances Data)

Usage

Type of Compound

Ester

Chiral Building Block

Yes

Starting Material

1,2-Pyrrolidinedicarboxylic acid

Pharmaceutical Industry

Commonly used as a starting material

1,1-Dimethylethyl Group

Present

Dimethylsilyl Group

Present

Stereochemistry

(2S,4S)

Applications

Synthesis of pharmaceuticals and agrochemicals

Ability

Creation of chiral centers and versatility as a building block in organic chemistry

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 87691-27-8 N-tert-butoxycarbonyl-L-cis-4-hydroxyproline 
• 288-32-4 1H-imidazole 

Downstream Products

• 119603-16-6 majusculamide D 
• 1404559-15-4 C₂₂H₃₀N₆OS 

Relevant articles and documents

HETEROCYCLIC COMPOUNDS FOR USE IN THE TREATMENT OF CANCER

The application relates to heterocyclic amide derivatives and their use in the treatment and prophylaxis of cancer, and to compositions containing said derivatives and processes for their preparation. (Formula (I))

DNA POLYMERASE THETA INHIBITORS

The invention relates to heterocyclic derivatives and their use in the treatment and prophylaxis of cancer, and to compositions containing said derivatives and processes for their preparation.

Highly Convergent Total Synthesis and Assignment of Absolute Configuration of Majusculamide D, a Potent and Selective Cytotoxic Metabolite from Moorea sp.

The total synthesis of majusculamide D (MJS-D) is described, a lipopentapeptide originally isolated from Lyngbya majuscula and reisolated from a Moorea sp. MJS-D possesses selective and potent cancer cell toxicity. A scalable and convergent strategy with a minimal number of purifications produced significant quantities of MJM-D for in vivo evaluations. The absolute configuration of the 1,3-dimethyl-octanamide motif was determined by synthesis of this fragment via ZACA chemistry.

ANTI-VIRAL COMPOUNDS

Compounds effective in inhibiting replication of Hepatitis C virus (“HCV”) are described. This invention also relates to processes of making such compounds, compositions comprising such compounds, and methods of using such compounds to treat HCV infection.

QUINAZOLIN-4-ONE DERIVATIVES

The invention relates to quinazolin-4-one compounds of the formula (I) and/or pharmaceutically acceptable salts and/or solvates thereof, Formula (I) wherein R1, R2, R3, R5, R6 and L are as defined in the description. Such compounds are suitable for the treatment of a disorder or disease which is mediated by the activity of the class I PI3K kinases.

ANTI-VIRAL COMPOUNDS

Compounds effective in inhibiting replication of Hepatitis C virus ("HCV") are described. This invention also relates to processes of making such compounds, compositions comprising such compounds, and methods of using such compounds to treat HCV infection.

Discovery and preclinical profile of teneligliptin (3-[(2S,4S)-4-[4-(3- methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl] thiazolidine): A highly potent, selective, long-lasting and orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes

Dipeptidyl peptidase IV (DPP-4) inhibition is suitable mechanism for once daily oral dosing regimen because of its low risk of hypoglycemia. We explored linked bicyclic heteroarylpiperazines substituted at the γ-position of the proline structure in the course of the investigation of l-prolylthiazolidines. The efforts led to the discovery of a highly potent, selective, long-lasting and orally active DPP-4 inhibitor, 3-[(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5- yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl]thiazolidine (8g), which has a unique structure characterized by five consecutive rings. An X-ray co-crystal structure of 8g in DPP-4 demonstrated that the key interaction between the phenyl ring on the pyrazole and the S2 extensive subsite of DPP-4 not only boosted potency, but also increased selectivity. Compound 8g, at 0.03 mg/kg or higher doses, significantly inhibited the increase of plasma glucose levels after an oral glucose load in Zucker fatty rats. Compound 8g (teneligliptin) has been approved for the treatment of type 2 diabetes in Japan.

Anti-Viral Compounds

Compounds effective in inhibiting replication of Hepatitis C virus (“HCV”) are described. This invention also relates to processes of making such compounds, compositions comprising such compounds, and methods of using such compounds to treat HCV infection.

Lead optimization of [(S)-γ-(arylamino)prolyl]thiazolidine focused on γ-substituent: Indoline compounds as potent DPP-IV inhibitors

Dipeptidyl peptidase IV (DPP-IV) inhibitors are looked to as a potential new antidiabetic agent class. A series of [(S)-γ-(arylamino)prolyl]thiazolidine compounds in which the electrophilic nitrile is removed are chemically stable DPP-IV inhibitors. To discover a structure for the γ-substituent of the proline moiety more suitable for interacting with the S2 pocket of DPP-IV, optimization focused on the γ-substituent was carried out. The indoline compound 22e showed a DPP-IV-inhibitory activity 100-fold more potent than that of the prolylthiazolidine 10 and comparable to that of NVP-DPP728. It also displayed improved inhibitory selectivity for DPP-IV over DPP8 and DPP9 compared to compound 10. Indoline compounds such as 22e have a rigid conformation with double restriction of the aromatic moiety by proline and indoline structures to promote interaction with the binding site in the S2 pocket of DPP-IV. The double restriction effect provides a potent inhibitory activity which compensates for the decrease in activity caused by removing the electrophilic nitrile.

INHIBITORS OF HEPATITIS C VIRUS PROTEASE, AND COMPOSITIONS AND TREATMENTS USING THE SAME

The present invention provides compounds of formula (I), (II) or (IV), or pharmaceutically acceptable salts and solvates thereof, which are useful as inhibitors of the Hepatitis C virus (HCV) protease enzyme and are also useful for the treatment of HCV infections in HCV--infected mammals, including humans. The present invention also provides pharmaceutical compositions comprising compounds of formula (I), (II) or (IV), their pharmaceutically acceptable salts and solvates. Furthermore, the present invention provides intermediate compounds and methods useful in the preparation of compounds of formulas (I), (II) and (IV).