115886-03-8

Basic information

• Product Name: 3-(benzyloxy)-5-methyl-4-isoxazolecarboxylic acid
• Synonyms: 3-(benzyloxy)-5-methyl-4-isoxazolecarboxylic acid
• CAS NO: 115886-03-8
• Molecular Weight: 233.224
• Mol File: 115886-03-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3-(benzyloxy)-5-methyl-4-isoxazolecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(benzyloxy)-5-methyl-4-isoxazolecarboxylic acid(115886-03-8)
• EPA Substance Registry System: 3-(benzyloxy)-5-methyl-4-isoxazolecarboxylic acid(115886-03-8)

Safety Data

• Hazardous Substances Data: 115886-03-8(Hazardous Substances Data)

Upstream product

• 67122-27-4 methyl 3-hydroxy-5-methyl-4-isoxazolecarboxylate 
• 22398-15-8 dimethyl 2-(1-methoxyethylidene)malonate 
• 113934-48-8 2-(1-Hydroxy-ethylidene)-malonic acid dimethyl ester 
• 100-39-0 benzyl bromide 
• 124-38-9 carbon dioxide 
• 115886-00-5 3-(benzyloxy)-5-methyl-1,2-oxazole 

Downstream Products

• 172540-13-5 3-(benzyloxy)-5-methyl-4-isoxazolecarbaldehyde 
• 172540-17-9 N-[(S)-(3-Benzyloxy-5-methyl-isoxazol-4-yl)-tert-butylcarbamoyl-methyl]-benzamide 
• 172540-16-8 N-[(R)-(3-Benzyloxy-5-methyl-isoxazol-4-yl)-tert-butylcarbamoyl-methyl]-benzamide 
• 172540-14-6 N-[(R)-(3-Benzyloxy-5-methyl-isoxazol-4-yl)-tert-butylcarbamoyl-methyl]-N-((S)-1-phenyl-ethyl)-benzamide 
• 172540-15-7 N-[(S)-(3-Benzyloxy-5-methyl-isoxazol-4-yl)-tert-butylcarbamoyl-methyl]-N-((S)-1-phenyl-ethyl)-benzamide 
• 172540-12-4 3-(benzyloxy)-5-methyl-4-isoxazolecarbonyl chloride 

Relevant articles and documents

Total synthesis of viridicatumtoxin B and analogues thereof: Strategy evolution, structural revision, and biological evaluation

The details of the total synthesis of viridicatumtoxin B (1) are described. Initial synthetic strategies toward this intriguing tetracycline antibiotic resulted in the development of key alkylation and Lewis acid-mediated spirocyclization reactions to form the hindered EF spirojunction, as well as Michael-Dieckmann reactions to set the A and C rings. The use of an aromatic A-ring substrate, however, was found to be unsuitable for the introduction of the requisite hydroxyl groups at carbons 4a and 12a. Applying these previous tactics, we developed stepwise approaches to oxidize carbons 12a and 4a based on enol- and enolate-based oxidations, respectively, the latter of which was accomplished after systematic investigations that revealed critical reactivity patterns. The herein described synthetic strategy resulted in the total synthesis of viridicatumtoxin B (1), which, in turn, formed the basis for the revision of its originally assigned structure. The developed chemistry facilitated the synthesis of a series of viridicatumtoxin analogues, which were evaluated against Gram-positive and Gram-negative bacterial strains, including drug-resistant pathogens, revealing the first structure-activity relationships within this structural type.

Excitatory Amino Acids. Improved Synthesis of Ibotenic Acid and X-Ray Analysis of an Unexpected Reaction Product, (RS)-N--3-oxobutyramide

A new synthesis of the excitotoxic natural product ibotenic acid (1) is described.Benzylation of 3-hydroxy-5-methylisoxazole (5) yielded 3-benzyloxy-5-methylisoxazole (7) and the isomeric isoxazol-3(2H)-one (6).While metallation of compound (7) by lithium