406220-14-2

Usage

Uses

Used in Pharmaceutical Synthesis:
Benzyl (S)-2-methyl-3-oxoazetidine-1-carboxylate is used as a building block in the synthesis of pharmaceuticals. Its chiral center provided by the (S)-2-methyl-3-oxoazetidine-1-carboxylate moiety makes it a valuable component in the preparation of chiral molecules, which are essential for the development of enantiomerically pure drugs with improved efficacy and reduced side effects.
Used in Agrochemical Synthesis:
In the agrochemical industry, benzyl (S)-2-methyl-3-oxoazetidine-1-carboxylate is also utilized as a building block for the synthesis of various agrochemicals. Its unique structure and properties contribute to the development of novel and effective compounds for crop protection and pest control.
Used as a Protecting Group in Organic Synthesis:
The benzyl group in benzyl (S)-2-methyl-3-oxoazetidine-1-carboxylate makes it suitable for use as a protecting group in organic synthesis. It helps control the reactivity of certain functional groups in chemical reactions, allowing for selective reactions and the synthesis of complex molecules with greater precision and yield.

Upstream product

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Relevant academic research and scientific papers

PYRAZOLO[1,5-A]PYRAZIN-4-YL DERIVATIVES

A compound compound having the structure: or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate of said compound or pharmaceutically acceptable salt, wherein A, A′ and A″ are independently O, C═O, C—R′ or N—R″, where R′ and R″ may independently be H, amino, —NR7COR6, COR6, —CONR7R8, C1-C6 alkyl, or hydroxy(C1-C6 alkyl), and R″ may be present or absent, and is present where the rules of valency permit, and where not more than one of A, A′ and A″ is O or C═O; R0 and R are independently H, Br, Cl, F, or C1-C6 alkyl; R1 is H, C1-C6 alkyl, or hydroxy(C1-C6 alkyl); R2 is selected from the group consisting of H, C1-C6 alkyl, C1-C6 alkoxy, hydroxy(C1-C6 alkyl), phenyl(C1-C6 alkyl), formyl, heteroaryl, heterocyclic, —COR6, —OCOR6, —COOR6, —NR7COR6, —CONR7R8, and —(CH2)n—W, where W is cyano, hydroxy, C3-C8 cycloalkyl, —SO2NR7R8, and —SO2—R9, where R9 is C1-C6 alkyl, C3-C8 cycloalkyl, heteroaryl, or heterocyclic; wherein each of said alkyl, cycloalkyl, heterocyclic, or heteroaryl may be unsubstituted or substituted by halo, cyano, hydroxy, or C1-C6 alkyl; X is C—R3 or N, where R3 may be H or C1-C6 alkyl; R4 and R5 are independently H, amino, C1-C6 alkyl, or hydroxy(C1-C6 alkyl); R6, R7 and R8 are each independently H, C1-C6 alkyl, C1-C4 alkoxy(C1-C6 alkyl), or C3-C8 cycloalkyl, said C1-C6 alkyl is optionally substituted by halo, CN or hydroxy; or, R7 and R8 together with the atom bonded thereto form a 5- or 6-membered ring, said ring being optionally substituted by halo, hydroxy, CN, or C1-C6 alkyl; and, n is 0, 1, 2 or 3. Also provided are methods of treatment as Janus Kinase inhibitors and pharmaceutical compositions containing the compounds of the invention and combinations thereof with other therapeutic agents.

1,5-rhodium shift in rearrangement of N -arenesulfonylazetidin-3-ols into benzosultams

Benzosultams are synthesized in an enantiopure form starting from α-amino acids through a rhodium-catalyzed rearrangement reaction of N-arenesulfonylazetidin-3-ols. Mechanistically, this reaction involves C-C bond cleavage by β-carbon elimination and C-H bond cleavage by a 1,5-rhodium shift.

Total synthesis of polyoximic acid

The structure and stereochemistry of polyoximic acid, a degradation product of polyoxins, was originally designated as trans-3-ethylidene-L-azetidine-2-carboxylic acid. However, total synthesis revealed that the correct structure was in fact cis-3-ethylidene-L-azetidine-2-carboxylic acid, which was confirmed by X-ray crystallography. The synthesis of the trans-isomer was also done and its identity was confirmed by X-ray analysis as well. The key step for constructing the four-membered ring was a rhodium catalyzed carbenoid insertion into the N - H bond of a β-amino acid derivative. The stereoselectivity of the exo-double bond was controlled by conducting a Horner-Emmons-Wadsworth or a Wittig reaction to generate the trans- and cis-isomers, respectively. Weinreb's amide was used as a latent methyl group for the separation of trans and cis mixtures. The double bond stereochemistry of polyoximic acid in the parent polyoxin was also confirmed to be cis by extensive 2D NMR studies.