1003013-76-0

Usage

Uses

Used in Pharmaceutical Industry:
3-((benzyloxy)methyl)oxetane is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its reactivity and structural flexibility allow for the creation of a wide range of drug molecules with potential therapeutic applications.
Used in Polymer Production:
3-((benzyloxy)methyl)oxetane is used as a monomer in the production of polymeric materials. Its unique structure contributes to the formation of polymers with specific properties, such as improved strength, flexibility, or chemical resistance, depending on the desired application.
Used in Research and Development:
3-((benzyloxy)methyl)oxetane is used as a research compound in the development of new chemical processes and materials. Its reactivity and structural properties make it an interesting candidate for studying reaction mechanisms, catalysts, and other aspects of organic chemistry.

Upstream product

• 100-39-0 benzyl bromide 
• 98-59-9 p-toluenesulfonyl chloride 
• 117087-18-0 2-((benzyloxy)methyl)propane-1,3-diol 

Relevant academic research and scientific papers

A Case Study in Catalyst Generality: Simultaneous, Highly-Enantioselective Br?nsted- And Lewis-Acid Mechanisms in Hydrogen-Bond-Donor Catalyzed Oxetane Openings

Generality in asymmetric catalysis can be manifested in dramatic and valuable ways, such as high enantioselectivity across a wide assortment of substrates in a given reaction (broad substrate scope) or as applicability of a given chiral framework across a variety of mechanistically distinct reactions (privileged catalysts). Reactions and catalysts that display such generality hold special utility, because they can be applied broadly and sometimes even predictably in new applications. Despite the great value of such systems, the factors that underlie generality are not well understood. Here, we report a detailed investigation of an asymmetric hydrogen-bond-donor catalyzed oxetane opening with TMSBr that is shown to possess unexpected mechanistic generality. Careful analysis of the role of adventitious protic impurities revealed the participation of competing pathways involving addition of either TMSBr or HBr in the enantiodetermining, ring-opening event. The optimal catalyst induces high enantioselectivity in both pathways, thereby achieving precise stereocontrol in fundamentally different mechanisms under the same conditions and with the same chiral framework. The basis for that generality is analyzed using a combination of experimental and computational methods, which indicate that proximally localized catalyst components cooperatively stabilize and precisely orient dipolar enantiodetermining transition states in both pathways. Generality across different mechanisms is rarely considered in catalyst discovery efforts, but we suggest that it may play a role in the identification of so-called privileged catalysts.

Highly Enantioselective, Hydrogen-Bond-Donor Catalyzed Additions to Oxetanes

A precisely designed chiral squaramide derivative is shown to promote the highly enantioselective addition of trimethylsilyl bromide (TMSBr) to a broad variety of 3-substituted and 3,3-disubstituted oxetanes. The reaction provides direct and general access to synthetically valuable 1,3-bromohydrin building blocks from easily accessed achiral precursors. The products are readily elaborated both by nucleophilic substitution and through transition-metal-catalyzed cross-coupling reactions. The enantioselective catalytic oxetane ring opening was employed as part of a three-step, gram-scale synthesis of pretomanid, a recently approved medication for the treatment of multidrug-resistant tuberculosis. Heavy-atom kinetic isotope effect (KIE) studies are consistent with enantiodetermining delivery of bromide from the H-bond-donor (HBD) catalyst to the activated oxetane. While the nucleophilicity of the bromide ion is expected to be attenuated by association to the HBD, overall rate acceleration is achieved by enhancement of Lewis acidity of the TMSBr reagent through anion abstraction.

Preparation method of 3-oxetane carboxylic acid

The invention provides a preparation method of 3-oxetane carboxylic acid. The preparation method is characterized by carrying out hydrolytic esterification reaction, hydrogen pulling reaction and reduction reaction by taking 3-hydroxypropionitrile as a raw material, thus obtaining 2-benzyloxymethyl-1,3-propanediol; carrying out cyclization reaction, debenzylation reaction and oxidation reaction on2-benzyloxymethyl-1,3-propanediol, thus obtaining 3-oxetane carboxylic acid. According to the preparation method of 3-oxetane carboxylic acid, provided by the invention, a key intermediate 2-benzyloxymethyl-1,3-propanediol can be prepared just through three-steps reaction by taking 3-hydroxypropionitrile as the raw material, and 3-oxetane carboxylic acid can be prepared just through six-steps reaction in a final integral route, so that the reaction route is greatly shortened, and reaction steps are reduced; compared with a preparation method requiring ten-steps reaction in the prior art, theyield is higher, the operation is easy, and industrial production can be favorably realized.

Pyrazole glucokinase activators

Disclosed herein are pyrazole glucokinase activators of the formula (I) useful for the treatment of metabolic diseases and disorders, preferably diabetes mellitus.