The first examples of SNAr-based macrocyclization: synthesis of model carboxylate-binding pockets of vancomycin
1994
Abstract
Model carboxylate-binding pocket C-O-D rings of vancomycin and related glycopeptides were efficiently synthesized by intramol. SNAr reactions. Thus, treatment of precursors I (R = H, 4-HOC6H4) with K2CO3 in DMF gave cyclic diaryl ethers II (R1 = NO2), with II (R = 4-HOC6H4) being a mixt. of atropisomers. II (R = H, R1 = NO2) was further converted into II (R = H, R1 = NH2, H, Cl). [on SciFinder (R)]
Details
Title
The first examples of SNAr-based macrocyclization: synthesis of model carboxylate-binding pockets of vancomycin
Author(s)
Beugelmans, Rene ; Zhu, Jieping ; Husson, Nicolas ; Bois-Choussy, Michele ; Singh, Girij Pal
Published in
Journal of the Chemical Society, Chemical Communications
Issue
4
Pages
439-40
Date
1994
ISSN
0022-4936
Keywords
Note
CAN 121:180167
34-3
Amino Acids, Peptides, and Proteins
Inst. Chim. Subst. Nat.,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
4530-20-5 (N-tert-Butoxycarbonylglycine); 27460-85-1 (N-tert-Butoxycarbonyl-D-(4-hydroxyphenyl)glycine) Role: RCT (Reactant), RACT (Reactant or reagent) (amidation of, with fluoro(nitro)phenethylamine); 621-37-4 (3-Hydroxyphenylacetic acid) Role: RCT (Reactant), RACT (Reactant or reagent) (amidation of, with glycine and arylglycine phenethylamides); 459-57-4 (4-Fluorobenzaldehyde) Role: PROC (Process) (conversion of, into fluoro(nitro)phenylacetonitrile); 157662-78-7P (4-Fluoro-3-nitrophenethylamine) Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and amidation of, with protected amino acids); 157662-72-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and intramol. nucleophilic arom. substitution of, atropisomers from); 157662-71-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and intramol. nucleophilic arom. substitution of, vancomycin C-D ring segment model from); 157662-73-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and redn. of, amino deriv. from); 157662-77-6P (4-Fluoro-3-nitrophenylacetonitrile) Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and selective redn. of, fluoro(nitro)phenethylamine from); 1404-90-6P (Vancomycin) Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of C-D ring segment of, via intramol. nucleophilic arom. substitution); 147949-75-5P; 157662-74-3P; 157662-76-5P; 157750-78-2P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, via intramol. nucleophilic arom. substitution); 157662-69-6P; 157662-70-9P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn., deblocking, and amidation of, with (hydroxyphenyl)acetic acid); 157662-75-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn., diazotization, and redn.or chlorination of)
34-3
Amino Acids, Peptides, and Proteins
Inst. Chim. Subst. Nat.,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
4530-20-5 (N-tert-Butoxycarbonylglycine); 27460-85-1 (N-tert-Butoxycarbonyl-D-(4-hydroxyphenyl)glycine) Role: RCT (Reactant), RACT (Reactant or reagent) (amidation of, with fluoro(nitro)phenethylamine); 621-37-4 (3-Hydroxyphenylacetic acid) Role: RCT (Reactant), RACT (Reactant or reagent) (amidation of, with glycine and arylglycine phenethylamides); 459-57-4 (4-Fluorobenzaldehyde) Role: PROC (Process) (conversion of, into fluoro(nitro)phenylacetonitrile); 157662-78-7P (4-Fluoro-3-nitrophenethylamine) Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and amidation of, with protected amino acids); 157662-72-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and intramol. nucleophilic arom. substitution of, atropisomers from); 157662-71-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and intramol. nucleophilic arom. substitution of, vancomycin C-D ring segment model from); 157662-73-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and redn. of, amino deriv. from); 157662-77-6P (4-Fluoro-3-nitrophenylacetonitrile) Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and selective redn. of, fluoro(nitro)phenethylamine from); 1404-90-6P (Vancomycin) Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of C-D ring segment of, via intramol. nucleophilic arom. substitution); 147949-75-5P; 157662-74-3P; 157662-76-5P; 157750-78-2P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, via intramol. nucleophilic arom. substitution); 157662-69-6P; 157662-70-9P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn., deblocking, and amidation of, with (hydroxyphenyl)acetic acid); 157662-75-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn., diazotization, and redn.or chlorination of)
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LSPN
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Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
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Peer-reviewed publications
Work outside EPFL
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Record creation date
2010-11-25