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Synthesis of a new triprotonated ligand and selective o-demethylation of methyl aryl ether by boron tribromide

✍ Scribed by N. Cheraïti; M.E. Brik

Book ID
104261569
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
212 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

Selective O-demethylation of the ortho methyl catecholate of N,N',N"-tris-(2,3dimethoxybenzeyl)-l,l,l-tris-(L-methioninemehyl)-ethane (2) has been accomplished by boron tribromide. The intramolecular nucleophilic attack of divalent sulphur on methyl enhance this cleavage, favours this selctivity and consequently afford the triprotonated ligand N,N',N'-tris-(2-hydroxy-3-methoxybenzoyl)-l,l,l-tris-(Lmethioninemethyl)-ethane ~ in a good yield.

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✍ Simon W. Breeden; Andrew Coop; Stephen M. Husbands; John W. Lewis 📂 Article 📅 1999 🏛 John Wiley and Sons 🌐 German ⚖ 59 KB 👁 2 views

In the pursuit of ring-constrained analogues of buprenorphine, we wished to prepare 6-O-demethylated analogues of the thevinols and orvinols. Previously it had been disclosed that lithium aluminum hydride (LAH) in THF containing a chlorinated solvent could achieve this transformation. Here we report