A SNAr based facile synthesis of triaryl diethers, degradation products of vancomycin and related glycopeptide antibiotics

A mild and efficient procedure has been developed for the synthesis of triaryl diethers and has been applied to the synthesis of diethers I (X1 = X2 = H; X1 = X2 = Cl; X1 = H, X2 = Cl), degrdn. products from glycopeptide antibiotics of the vancomycin family. Thus, regioselective reaction of Me gallate and Me 3-nitro-4-fluorobenzoate with added K2CO3 in DMF afforded a functionalized triaryl ether which was readily converted to diethers I (X1 = X2 = H; X1 = X2 = Cl). Alternatively, protection of Me gallate with Ph2CCl2, followed by sequential reactions with the benzoate and base via various intermediates afforded diether I (X1 = H, X2 = Cl). [on SciFinder (R)]


Published in:
Tetrahedron Letters, 34, 48, 7741-4
Year:
1993
Keywords:
Note:
CAN 120:269764
25-18
Benzene, Its Derivatives, and Condensed Benzenoid Compounds
Inst. Chim. Subst. Nat.,CNRS,Gif-sur-Yvette,Fr.
Journal
0040-4039
written in English.
154492-17-8P Role: PREP (Preparation) (formation and reaction of, with Me gallate, triaryl diether from); 154492-19-0P; 154492-21-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and deamination of); 154492-26-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and deamination-chlorination of); 154492-22-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and deprotection of); 154492-20-3P; 154492-25-8P; 154492-27-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and nitrate redn. of); 69829-46-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and reaction of, with fluoronitrobenzoate); 154492-23-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and reaction with fluoronitrobenzoate, triaryl diether from); 154492-18-9P; 154492-24-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and O-methylation of); 55033-62-0P; 57466-23-6P; 70734-92-8P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 329-59-9 (Methyl 4-fluoro-3-nitrobenzoate) Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with Me gallate, triaryl diether from); 99-24-1 (Methyl gallate) Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with fluoronitrobenzoate, triaryl diether from)
Laboratories:




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