1036407-25-6

Basic information

• Product Name: [(1r, 3R, 4S)-3,4-difluorocyclopentyl]methanol
• Synonyms: [(1r, 3R, 4S)-3,4-difluorocyclopentyl]methanol
• CAS NO: 1036407-25-6
• Molecular Weight: 136.142
• Mol File: 1036407-25-6.mol

Chemical Properties

• CAS DataBase Reference: [(1r, 3R, 4S)-3,4-difluorocyclopentyl]methanol(CAS DataBase Reference)
• NIST Chemistry Reference: [(1r, 3R, 4S)-3,4-difluorocyclopentyl]methanol(1036407-25-6)
• EPA Substance Registry System: [(1r, 3R, 4S)-3,4-difluorocyclopentyl]methanol(1036407-25-6)

Safety Data

• Hazardous Substances Data: 1036407-25-6(Hazardous Substances Data)

Upstream product

• 233588-82-4 trans-3,4-epoxy-1-cyclopentanecarboxylic acid ethyl ester 
• 21622-01-5 ethyl 3-cyclopentene-1-carboxylate 
• 7686-77-3 3-cyclopentene-1-carboxylic acid 
• 1036407-23-4 [(1α,3α,4α)-3,4-difluorocyclopentyl]methyl benzoate 

Relevant articles and documents

Practical and Scalable Synthesis of a Glucokinase Activator via One-Pot Difluorination and Julia Olefination

We describe the process research and development of a practical synthesis of glucokinase activator 1 as a potential drug for treating type 2 diabetes mellitus. The key structure, a 3,4-cis-difluorinated cyclopentane moiety, was constructed via diastereoselective epoxidation, followed by one-pot difluorination with Et3N·3HF and perfluorobutanesulfonyl fluoride (PBSF). Julia olefination of benzothiazol-2-yl sulfone with glyoxylate furnished an E/Z mixture of acrylate, followed by isomerization of the alkene to the desired E configuration during the formation of the acid chloride in the final step. This development achieved a highly practical process route to 1 (15percent overall yield, 12 steps). This process route overcomes the drawbacks of the original medicinal chemistry synthetic route, which used hazardous and costly reagents (LiAlH4, OsO4, and Deoxo-Fluor) and had low efficiency (4percent overall yield, 20 steps).

CYCLOPENTYLACRYLIC ACID AMIDE DERIVATIVE

A compound having a hypoglycemic effect is provided. The compound and a pharmaceutically acceptable salt thereof are useful for the treatment or prevention of diabetes, obesity, and the like. The compound is represented by the general formula (1): (wherein R1 and R2 are each independently a hydrogen atom, a halogen atom, an amino group, a hydroxyl group, a hydroxyamino group, a nitro group, a cyano group, a sulfamoyl group, a C1 to C6 alkyl group, a C1 to C6 alkoxy group, a C1 to C6 alkylsulfonyl group, a C1 to C6 alkylsulfinyl group, a C1 to C6 alkylsulfonyl group, or a C1 to C6 alkoxy-C1 to C6 alkylsulfonyl group, and A is a substituted or unsubstituted heteroaryl group).

GLUCOKINASE ACTIVATOR

A compound, or a pharmaceutically acceptable salt thereof, represented by the formula (1), (wherein, the carbon atom marked with an * is in the R-configuration, R1 represents a hydrogen atom, a halogen atom, an amino group, a hydroxyl group, a hydroxyamino group, a nitro group, a cyano group, a sulfamoyl group, a C1-C6 alkyl group, or a C1-C6 alkoxy group, R2 represents a C3-C6 cycloalkylsulfanyl group, a C3-C6 cycloalkylsulfinyl group, or a C3-C6 cycloalkylsulfonyl group, and A represents a substituted or unsubstituted heteroaryl group).