2552-53-6

Usage

Uses

Used in Pharmaceutical and Biologically Active Compounds Synthesis:
3-(Benzyloxy)isoxazole-5-carbaldehyde is utilized as a key building block in the synthesis of various pharmaceuticals and biologically active compounds. Its unique structure and reactivity contribute to the development of new molecules with desired properties and applications in the medical field.
Used in Medicinal Chemistry for Antimicrobial and Antiviral Applications:
In the field of medicinal chemistry, 3-(Benzyloxy)isoxazole-5-carbaldehyde is recognized for its potential antimicrobial and antiviral activities. Its ability to target and inhibit the growth of harmful microorganisms and viruses makes it a valuable compound for the development of new treatments and therapies.
Used in Organic Synthesis:
3-(Benzyloxy)isoxazole-5-carbaldehyde is employed as a versatile intermediate in organic synthesis, allowing for the creation of a wide range of chemical compounds with diverse applications. Its unique structure and reactivity make it an essential tool for chemists in designing and synthesizing new molecules for various industries.

InChI:InChI=1/C11H9NO3/c13-7-10-6-11(12-15-10)14-8-9-4-2-1-3-5-9/h1-7H,8H2

Upstream product

• 2552-54-7 3-(benzyloxy)isoxazole-5-carboxylic acid 
• 67-68-5 dimethyl sulfoxide 
• 123320-44-5 (3-(benzyloxy)isoxazol-5-yl)methanol 
• 205115-22-6 3-benzyloxyisoxazole-5-carboxylic acid methyl ester 
• 100-39-0 benzyl bromide 
• 16446-44-9 3-benzyloxy-5-diethoxymethyl-isoxazole 
• 100-51-6 benzyl alcohol 

Downstream Products

• 5777-21-9 3-oxo-2,3-dihydro-isoxazole-5-carbaldehyde 
• 951698-14-9 C₁₃H₁₃NO₃ 
• 951698-16-1 C₁₃H₁₃NO₃ 
• 1383851-44-2 ethyl (2E)-3-[3-(benzyloxy)-1,2-oxazol-5-yl]acrylate 
• 1383851-45-3 3-[3-(benzyloxy)-1,2-oxazol-5-yl]propan-1-ol 
• 951698-18-3 C₁₅H₁₅NO₄ 
• 1383851-47-5 3-[3-(benzyloxy)-1,2-oxazol-5-yl]propyl 4-methylbenzenesulfonate 
• 1383851-48-6 N-{3-[3-(benzyloxy)-1,2-oxazol-5-yl]propyl}-N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)-1-benzofuran-6-yl]methanesulfonamide 
• 2552-51-4 (3-benzyloxy-isoxazol-5-yl)-hydroxy-acetic acid ethyl ester 
• 2552-52-5 (3-benzyloxy-isoxazol-5-yl)-hydroxy-acetonitrile 
• 951698-15-0 C₁₅H₁₈N₂O₂ 
• 951698-19-4 C₁₅H₁₇IN₂O₂ 

Relevant academic research and scientific papers

Process Research and Development of an Enantiomerically Enriched Allyic Amine, One of the Key Intermediates for the Manufacture of Synthetic Tetracyclines

A robust, cost-effective, and high yielding manufacturing process for enantiomerically enriched (S)-allylic amine 3, a key intermediate for fully synthetic tetracyclines have been developed. Two novel and scalable asymmetric vinylations resulting in high-to-excellent stereoselectivity have been developed for the key step. The final product is purified by an efficient crystallization of a l-tartaric salt. The process described has been used to manufacture ～350 kg of the tartaric salt of 3 with 99.0% ee in 8 steps (35% overall yield) from cheap and readily available dimethyl maleate.

HEPATITIS C INHIBITORS AND USES THEREOF

This disclosure relates to: (a) compounds and salts thereof that, inter alia, inhibit HCV; (b) intermediates useful for the preparation of such compounds and salts; (c) compositions comprising such compounds and salts; (d) methods for preparing such intermediates, compounds, salts, and compositions; (e) methods of use of such compounds, salts, and compositions; and (f) kits comprising such compounds, salts, and compositions.

Evaluation of protecting groups for 3-hydroxyisoxazoles - Short access to 3-alkoxyisoxazole-5-carbaldehydes and 3-hydroxyisoxazole-5-carbaldehyde, the putative toxic metabolite of muscimol

The regioselectivity of the 3-hydroxyisoxazole-5-ester 1 is studied with respect to O- versus N-alkylation. 3-O-Alkyl products 2 are highly favoured with benzyl, benzhydryl, and allyl bromide (≥ 91:9), in contrast to known uses of 5-alkyl-3-hydroxyisoxazoles or when methylation with diazomethane (or methyl iodide) is effected. Methoxymethylation leads to the N-substituted isoxazolinone 3e only. On reduction with DIBAH, the esters 2 afford 3-O-protected 3-hydroxyisoxazole-5-carbaldehydes 4 (75-98%). For removal of the benzyl protecting groups, three variations (HBr/HOAc, H2/ Pd/BaSO4, NBS/AIBN) were found useful with 5-ester, 5-formyl, and 5-hydroxymethyl derivatives. The free 3-hydroxy-5-carbaldehyde 9, the putative toxic metabolite of the GABA agonist muscimol, is prepared accordingly. The O-protected 3-hydroxyisoxazole-5-carbaldehydes 4 constitute versatile intermediates in various routes to analogues of CNS-active amino acids and can now be obtained in a highly efficient manner.