1456616-42-4

Basic information

• Product Name: tert-butyl ((2S,3R)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate
• Synonyms: tert-butyl ((2S,3R)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate;N-[(2S,3R)-2-(2,5-Difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester;Omarigliptin Impurity 4
• CAS NO: 1456616-42-4
• Molecular Formula: C₁₆H₁₉F₂NO₄
• Molecular Weight: 327.3231664
• EINECS: -0
• Mol File: 1456616-42-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 433.4±45.0 °C(Predicted)
• Appearance: /
• Density: 1.25±0.1 g/cm3(Predicted)
• PKA: 11.00±0.40(Predicted)
• CAS DataBase Reference: tert-butyl ((2S,3R)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl ((2S,3R)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate(1456616-42-4)
• EPA Substance Registry System: tert-butyl ((2S,3R)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate(1456616-42-4)

Safety Data

• Hazardous Substances Data: 1456616-42-4(Hazardous Substances Data)

Usage

Description

Tert-butyl ((2S,3R)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate is a chemical compound that serves as an analog of Omarigliptin (O633100), which is a potent and selective dipeptidyl peptidase 4 (DPP-4) inhibitor. tert-butyl ((2S,3R)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate is characterized by its ability to inhibit DPP-4, a key enzyme involved in the regulation of glucose levels in the body.

Uses

Used in Pharmaceutical Industry:
Tert-butyl ((2S,3R)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate is used as a therapeutic agent for the treatment of type 2 diabetes. Its application is based on its ability to inhibit the DPP-4 enzyme, which plays a crucial role in the regulation of glucose levels in the body. By inhibiting DPP-4, this compound can help improve glycemic control and provide a potential treatment option for patients with type 2 diabetes.
Additionally, as an analog of Omarigliptin, it may also be used in the development of new drugs or therapies targeting DPP-4 for various medical conditions related to glucose metabolism and other potential applications in the pharmaceutical industry.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 951127-26-7 1-(2,5-difluorophenyl)-2-nitroethanol 
• 2646-90-4 2,5-difluorobenzaldehyde 
• 1456616-39-9 C₁₂H₁₁F₂NO₃ 
• 951127-28-9 6-(2,5-difluorophenyl)-3-methylidene-5-nitro-3,4-dihydro-2H-pyran 
• 35730-09-7 2,5-difluorobenzoyl chloride 
• 951127-27-8 1-(2,5-difluorophenyl)-2-nitroethanone 

Downstream Products

• 1456616-64-0 C₁₆H₁₈F₂N₄O 
• 1456616-65-1 C₁₆H₁₈F₂N₄O 

Relevant articles and documents

A preparation method of the compounds

The invention discloses a preparation method of a compound. The preparation method comprises the steps: carrying out chemical resolution on a compound 3 namely 5-amino-6-(2,5-difluorophenyl)-tetrahydro-2H-pyran-3-ol, to obtain a salt formed from the compound 3 and a resolving agent; carrying out chemical combination of the salt formed from the compound 3 and the resolving agent with di-tert-butyl dicarbonate in an alkali liquid to obtain a compound 4; and oxidizing hydroxyl of the compound 4 to obtain a compound N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]-carbamic acid 1,1-dimethylethyl ester represented by the formula I. According to the preparation method, by selecting the low-price raw materials, the synthetic route is shortened, asymmetric hydrogenation reaction steps are omitted, and thus the production cost is greatly reduced, and the yield is significantly improved.

Novel tetrahydropyran analogs as dipeptidyl peptidase IV inhibitors: Profile of clinical candidate (2R,3S,5R)-2-(2,5-difluorophenyl)-5-[2- (methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran- 3-amine (23)

A series of novel tri-2,3,5-substituted tetrahydropyran analogs were synthesized and evaluated as inhibitors of dipeptidyl peptidase IV (DPP-4) for the treatment of type 2 diabetes. Optimization of the series provided inhibitors with good DPP-4 potency and selectivity over other peptidases (QPP, DPP8, and FAP). Compound 23, which is very potent, selective, efficacious in the diabetes PD model, and has an excellent pharmacokinetic profile, is selected as a clinical candidate.