86334-63-6

Usage

Uses

Used in Pharmaceutical Industry:
Benzyl((2S,3S)-1-(2,4-dimethoxybenzyl)-2-(hydroxymethyl)-4-oxoazetidin-3-yl)carbamate is used as a potential drug candidate or a precursor for drug synthesis due to its complex structure and the presence of functional groups that may exhibit biological activity or binding affinity to specific targets.
Used in Medicinal Chemistry Research:
benzyl((2S,3S)-1-(2,4-dimethoxybenzyl)-2-(hydroxymethyl)-4-oxoazetidin-3-yl)carbamate is utilized in medicinal chemistry research to explore its potential as a lead compound for the development of new pharmaceuticals, given its unique structural features and the possibility of interacting with biological targets.

Upstream product

• 86299-41-4 (3S,4S)-3-(benzyloxycarboxamido)-1-(2,4-dimethoxybenzyl)-4-formyl-2-azetidinone 
• 86299-39-0 N-[(3S,4S)-cis-1-(2,4-dimethoxybenzyl)-4-formyl-2-oxo-3-azetidinyl]phthalimide 
• 501-53-1 benzyl chloroformate 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 
• 86334-59-0 benzyl ((2S,3S)-1-(2,4-dimethoxybenzyl)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-oxoazetidin-3-yl)-carbamate 
• 86334-58-9 (3S,4S)-3-amino-1-(2,4-dimethoxybenzyl)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)azetidin-2-one 
• 86390-73-0 N-<(3S,4S)-cis-1-(2,4-dimethoxybenzyl)-4-<(R)-2,2-dimethyl-1,3-dioxalan-4-yl>-2-oxo-3-azetidinyl>phthalimide 
• 20781-20-8 2,4-Dimethoxybenzylamine 
• 88852-09-9 (R,E)-1-(2,4-dimethoxyphenyl)-N-((2,2-dimethyl-1,3-dioxolan-4-yl)methylene)methanamine 

Downstream Products

• 99397-29-2 (3S,4S)-3-benzyloxycarbonylamino-4-hydroxymethyl-2-azetidinone 

Relevant academic research and scientific papers

Process Development for the Synthesis of a Monobactam Antibiotic-LYS228

A scalable process for the novel monobactam antibiotic LYS228 has been developed. This paper covers a novel scalable process for producing β-lactam 10 in the multiple kilogram scale. An alternative approach to compound 7 without protecting-group exchange

MONOBACTAM ORGANIC COMPOUNDS FOR THE TREATMENT OF BACTERIAL INFECTIONS

This invention pertains generally to antibacterial compounds of Formula I, as further described herein, and pharmaceutically acceptable salts and formulations thereof. In certain aspects, the invention pertains to methods of using such compounds to treat infections such as those caused by Gram-negative bacteria.

Chiral azetidinone epoxides

Epoxyimines, formed from epoxyaldehydes, react via cycloaddition with amino-protected glycyl halides to provide 3-protected-amino-4-(substituted oxiranyl)azetidinones represented by the formula STR1 wherein, e.g., R is protected amino; R1 and R2 is H, alkyl, phenyl, etc.; and R3 inter alia a nitrogen-protecting group. Chiral epoxyimines from chiral epoxyaldehydes induce high levels of asymmetric induction during the cycloaddition to provide substantially one diastereomer of the 3,4-disubstituted azetidinone. For example, the epoxyimine formed with (2R,3S)-2-formyl-3-phenyloxirane and 2,4-dimethoxybenzylamine is reacted with phthalimidoacetyl chloride to provide [3R,4R,4(2S,3S]-1-(2,4-dimethoxybenzyl)-3-phthalimido-4-(3-phenyloxiran-2-yl)-2-azetidinone. The epoxy-substituted azetidinones are useful intermediates for β-lactam antibiotic compounds.

An Examination of O-2-Isocephems as Orally Absorbable Antibiotics

The synthesis and structure-activity relationships of a series of orally absorbed O-2-isocephems are described.These compounds possessed a D-amino substituent at the 7-position while the substituent at the 3-position was varied.Relative to the analogous cephems, the O-2-isocephems exhibited comparable to better activity against Gram-positive organisms.Against Gram-negative organisms, their activity was variable but did indicate a lower β-lactamase stability.Following oral administration, the O-2-isocephems generally exhibited longer half-lives but lower Cmax's and urinary recoveries.