76417-04-4

Usage

Uses

Used in Medical Applications:
Virantmycin is used as an antibiotic for treating a range of bacterial infections, including skin and soft tissue infections, pneumonia, and sexually transmitted diseases. Its broad-spectrum activity allows it to target a wide range of bacteria, making it a versatile treatment option.
Used in Pharmaceutical Industry:
Virantmycin is used as a pharmaceutical agent for its broad-spectrum antibacterial properties, commonly administered orally or through intravenous injection. It is valued for its effectiveness in treating various infections and for being generally well-tolerated, although it may cause side effects in some individuals such as nausea, vomiting, diarrhea, or allergic reactions.

Upstream product

• 141410-06-2 (S)-indoline-2-carboxylic acid methyl ester 
• 197460-36-9 methyl (S)-N-(tert-butoxycarbonyl)indoline-2-carboxylate 
• 78983-16-1 (+/-)-virantmycin methyl ester 
• 104784-18-1 5,6-dimethyl-1-methoxyhept-5-en-2-one 
• 104784-19-2 6,7-dimethyl-3-methoxymethyloct-6-en-1-yn-3-ol 
• 104784-23-8 2-(3,4-Dimethyl-pent-3-enyl)-2-methoxymethyl-1,2-dihydro-quinoline-6-carboxylic acid methyl ester 
• 104784-25-0 methyl N-formyl-2-(3,4-dimethyl-3,4-epoxypentyl)-3-hydroxy-2-(methoxymethyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate 
• 104784-22-7 methyl N-formyl-2-(3,4-dimethyl-3,4-epoxypentyl)-3,4-epoxy-2-(methoxymethyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate 
• 5072-70-8 1-bromo-2,3-dimethyl-2-butene 
• 619-45-4 4-methoxycarbonyl aniline 
• 104784-27-2 methyl N-formyl-2-(3,4-dimethylpent-3-enyl)-3-hydroxy-2-(methoxymethyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate 
• 104784-24-9 methyl N-formyl-1,2-dihydro-2-(3,4-dimethylpent-3-enyl)-2-(methoxymethyl)quinoline-6-carboxylate 
• 104784-21-6 methyl 3-(6,7-dimethyl-3-hydroxy-3-methoxymethyloct-6-en-1-ynyl)-4-aminobenzoate 
• 104784-26-1 methyl 2-(3,4-dimethylpent-3-enyl)-3-hydroxy-2-(methoxymethyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate 

Relevant academic research and scientific papers

Stereospecific construction of contiguous quaternary and tertiary stereocenters by rearrangement from indoline-2-methanol to 2,2,3-trisubstituted tetrahydroquinoline: Application to an efficient total synthesis of natural virantmycin

Only nine steps away: PPh3/CCl4-mediated stereospecific rearrangement of α,α-disubstituted indoline-2-methanol to 2,2,3-trisubstituted optically active tetrahydroquinoline (see scheme) has been developed. The reaction was applied to

Stereospecific synthesis of 2,2,3-trisubstituted tetrahydroquinolines: Application to the total syntheses of benzastatin E and natural virantmycin

An efficient methodology for the synthesis of 2,2,3-trisubstituted tetrahydroquinolines has been developed, which involves the triphenylphosphine- CCl4-mediated stereospecific rearrangement of α,α- disubstituted indoline-2-methanols 15 to 2,2,3-trisubstituted tetrahydroquinolines 26. The rearrangement precursors 15 are readily prepared by the diastereoselective Grignard addition to 2-acylindolines 13. The total syntheses of (+)-benzastatin E (1) and natural virantmycin (2a) were accomplished utilizing this methodology. This rearrangement reaction might afford some chemical precedent for the biogenetic pathway of the benzastatin family.

A simple convergent approach to the synthesis of the antiviral agent virantmycin

Formula presented The antiviral agent (±)-virantmycin has been synthesized from two simple building blocks (2 and 3) in eight steps, as outlined in Scheme 2.

Synthetic studies on virantmycin. 1. Total synthesis of (±)-virantmycin and determination of its relative stereochemistry

The efficient and stereospecific route to the tetrahydroquinoline ring models 3 and 4 of virantmycin has been developed by means of an intramolecular nitrene addition reaction as a key step. In the NOE experiments of 4 and 3 we revealed that a ring invers

TOTAL SYNTHESIS OF THE ANTIVIRAL (+/-)-VIRANTMYCIN

The total synthesis of the racemic modification of the antiviral metabolite virantmycin is described starting from p-aminobenzoic acid and utilising acetylenic precursors.