TARTARIC ACID AND ITS<i>O</i>-ACYL DERIVATIVES. PART 1. SYNTHESIS OF TARTARIC ACID AND<i>O</i>-ACYL TARTARIC ACIDS AND ANHYDRIDES

Bernaś, Urszula; Ruśkowski, Paweł; Synoradzki, Ludwik

doi:10.1080/00304940509355401

Cited by 23 publications

(8 citation statements)

References 79 publications

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“…Synthesis of di- tert -butyl l -tartrate ( 18 ) from l -tartaric acid was achieved via O , O ′-diacetyl l -tartaric anhydride ( 15 ), O , O ′-diacetyl l -tartaric acid ( 16 ), and O , O ′-diacetyl-di- tert -butyl l -tartrate ( 17 ) according to literature procedures. − Characterization data matched literature reports for 15 , 16 , 17 , and 18 . Coupling reactions of chloroacetyl hydroxycinnamate ( 13 or 14 ) with 18 to give 19 or 21 were achieved in a fashion analogous to that of a previous paper …”

Section: Materials and Methodsmentioning

confidence: 81%

Hydroxycinnamoyl Glucose and Tartrate Esters and Their Role in the Formation of Ethylphenols in Wine

Hixson

Hayasaka

Curtin

et al. 2016

J. Agric. Food Chem.

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Synthesized p-coumaroyl and feruloyl l-tartrate esters were submitted to Brettanomyces bruxellensis strains AWRI 1499, AWRI 1608, and AWRI 1613 to assess their role as precursors to ethylphenols in wine. No evolution of ethylphenols was observed. Additionally, p-coumaroyl and feruloyl glucose were synthesized and submitted to B. bruxellensis AWRI 1499, which yielded both 4-ethylphenol and 4-ethylguaiacol. Unexpected chemical transformations of the hydroxycinnamoyl glucose esters during preparation were investigated to prevent these in subsequent synthetic attempts. Photoisomerization gave an isomeric mixture containing the trans-esters and undesired cis-esters, and acyl migration resulted in a mixture of the desired 1-O-β-ester and two additional migrated forms, the 2-O-α- and 6-O-α-esters. Theoretical studies indicated that the photoisomerization was facilitated by deprotonation of the phenol, and acyl migration is favored during acidic, nonaqueous handling. Preliminary LC-MS/MS studies observed the migrated hydroxycinnamoyl glucose esters in wine and allowed for identification of feruloyl glucose in red wine for the first time.

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Section: Materials and Methodsmentioning

confidence: 81%

Hydroxycinnamoyl Glucose and Tartrate Esters and Their Role in the Formation of Ethylphenols in Wine

Hixson

Hayasaka

Curtin

et al. 2016

J. Agric. Food Chem.

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“…White crystal: mp 196–198 °C [Lit. 43 mp 195–199 °C], 1 H NMR (CDCl 3 , 400 MHz): δ 6.02 (s, 2H), 7.54 (t, J = 7.8 Hz, 4H), 7.70 (t, J = 7.5 Hz, 2H), 8.12 (d, J = 7.1 Hz, 4H); 13 C NMR (CDCl 3 , 101 MHz): δ 165.5, 163.5, 134.7, 130.4, 128.8, 127.2, 72.9.…”

Section: Methodsmentioning

confidence: 99%

Resolution of Racemic α-Hydroxyphosphonates: Bi(OTf)₃-Catalyzed Stereoselective Esterification of α-Hydroxyphosphonates with (+)-Dibenzoyl-l-tartaric Anhydride

et al. 2019

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A practical and efficient method has been developed for the preparation of optically active α-hydroxyphosphonates through resolution of the racemates. Treatment of racemic diethyl 1-hydroxy-1-phenylmethylphosphonate (1) with (+)-dibenzoyl-L-tartaric anhydride gave two diastereomeric esters 2 and 3 in the presence of bismuth triflate (15 mol %) in an 86:14 ratio. The two diastereomeric esters were separated by simple column chromatography, and the structure for the major diastereomer was determined by X-ray crystallographic analysis. Simple hydrolysis of the isolated major diastereomer in the usual manner afforded (R)-O,O-diethyl-1-[hydroxyl(phenyl)methyl] phosphonate 1. The advantages of the present method are that the operation is simple and easy to handle, along with rapid and good yield preparations of both enantiomers of the racemic α-phosphonates 1. Diastereoselective reactions of various racemic α-hydroxyphosphonates with d-Bz-L-TA in the presence of Bi(OTf)3 are also described.

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“…However, due to the difficult resolution by crystallization and the necessity of column chromatography, this method is of little preparative importance as a source of monoacyl-N-substituted tartrimides. To check the reaction course of diacyltartaric acids with primary amines, we synthesized the compounds which may occur in the reaction system of dibenzoyltartaric acid 1a and benzyl amine 2f, i. e. dibenzoyl-N-benzyl-tartaric monoamide 7f 16 from dibenzoyltartaric anhydride, 17 dibenzoyl-N,N′-dibenzyltartaric diamide 8f 16 from 1a, 17 mixture of isomeric monobenzoyl-Nbenzyltartaric monoamides 10f′ and 10f″ 17 from monobenzoyltartaric anhydride, 18 and dibenzoyl-N-benzyltartrimide 4f 19 from N-benzyltartrimide. Then, we examined the reaction of dibenzoyltartaric acid with benzyl amine (1:1 molar ratio) (HPLC) under azeotropic distillation of water.…”

Section: Resultsmentioning

confidence: 99%

Tartaric acid and its O-acyl derivatives. Part 8. Direct synthesis of novel N-substituted mono- and diacyltartrimides: unusual reaction course

Ruśkowski¹,

Synoradzki

Włostowski³

2011

Arkivoc

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TARTARIC ACID AND ITSO-ACYL DERIVATIVES. PART 1. SYNTHESIS OF TARTARIC ACID ANDO-ACYL TARTARIC ACIDS AND ANHYDRIDES

Cited by 23 publications

References 79 publications

Hydroxycinnamoyl Glucose and Tartrate Esters and Their Role in the Formation of Ethylphenols in Wine

Hydroxycinnamoyl Glucose and Tartrate Esters and Their Role in the Formation of Ethylphenols in Wine

Resolution of Racemic α-Hydroxyphosphonates: Bi(OTf)₃-Catalyzed Stereoselective Esterification of α-Hydroxyphosphonates with (+)-Dibenzoyl-l-tartaric Anhydride

Tartaric acid and its O-acyl derivatives. Part 8. Direct synthesis of novel N-substituted mono- and diacyltartrimides: unusual reaction course

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TARTARIC ACID AND ITSO-ACYL DERIVATIVES. PART 1. SYNTHESIS OF TARTARIC ACID ANDO-ACYL TARTARIC ACIDS AND ANHYDRIDES

Cited by 23 publications

References 79 publications

Hydroxycinnamoyl Glucose and Tartrate Esters and Their Role in the Formation of Ethylphenols in Wine

Hydroxycinnamoyl Glucose and Tartrate Esters and Their Role in the Formation of Ethylphenols in Wine

Resolution of Racemic α-Hydroxyphosphonates: Bi(OTf)3-Catalyzed Stereoselective Esterification of α-Hydroxyphosphonates with (+)-Dibenzoyl-l-tartaric Anhydride

Tartaric acid and its O-acyl derivatives. Part 8. Direct synthesis of novel N-substituted mono- and diacyltartrimides: unusual reaction course

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Resolution of Racemic α-Hydroxyphosphonates: Bi(OTf)₃-Catalyzed Stereoselective Esterification of α-Hydroxyphosphonates with (+)-Dibenzoyl-l-tartaric Anhydride