New highly regioselective reactions of unprotected sucrose. Synthesis of 2-O-acylsucroses and 2-O-(N-alkylcarbamoyl)sucroses

Chauvin, Caroline; Baczko, Krystyna; Plusquellec, Daniel

doi:10.1021/jo00060a053

Cited by 70 publications

(25 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The P-N-glucosyl-N-heptylurea (GHU) and the 2-0-lauroyl saccharose (LS) were provided by Professor Plusquellec (14,15). The critical micellar concentrations (CMC) of these nonionic surfactants are given in Table 1.…”

Section: Methodsmentioning

confidence: 99%

Electrochemical and spectroscopic behavior of trifluoromethylacetophenone in aqueous and micellar medium

Liotier¹,

Mousset²,

Mousty³

1995

Can. J. Chem.

View full text Add to dashboard Cite

The electrochemical behavior of 4-trifluoromethylacetophenone (TFMA) has been studied in aqueous (2 ≤ pH ≤ 10), micellar, and ethanolic solutions using polarographic techniques. A slow hydration process of the carbonyl group has been observed by means of polarography and UV–visible spectrophotometry. Besides the well-known pH dependence of the electroreduction of aromatic ketones, C—F bond cleavages concomitant to the ketone reduction occur under electrolysis conditions in alkaline medium (pH = 10) at a very negative potential (−1.7 V), leading to the formation of 4-methylacetophenone, which is reduced at this potential with formation of the carbinol and of symmetrical and dissymmetrical pinacols. Finally, the reduction of TFMA has been performed in the presence of chiral surfactants in order to test their ability to induce an asymmetric induction. Keywords: 4-trifluoromethylacetophenone, 4-methylacetophenone, electroreduction, micellar medium, chiral surfactants, hydration, C—F bond fission.

show abstract

Section: Methodsmentioning

confidence: 99%

Electrochemical and spectroscopic behavior of trifluoromethylacetophenone in aqueous and micellar medium

Liotier¹,

Mousset²,

Mousty³

1995

Can. J. Chem.

View full text Add to dashboard Cite

show abstract

“…They have been synthesized by selective chemical synthesis, using the Mitsunobu reaction, leading to the isomers in position 6 as the main product, by enzymatic synthesis mainly giving the 1 isomer by the usual transesterification reaction, leading to mixtures containing mainly the isomers on the three primary positions (Fig. 1), or by using thiazolidinethioneactivated esters [25]. On some occasions, the regioisomers have been purified by preparative HPLC, leading to highly pure regioisomers.…”

Section: Introductionmentioning

confidence: 99%

PFGSE–NMR study of the self-diffusion of sucrose fatty acid monoesters in water

Molinier

Fenêt

Fitremann

et al. 2005

Journal of Colloid and Interface Science

View full text Add to dashboard Cite

“…Nevertheless, several one-step procedures for the regioselective chemical acylation of sucrose have been described. They are based on the use of exceptionally mild reaction conditions (Khan, 1984), sterically hindered acid chlorides (Chowdhary et al, 1984), activated sucrose following the Mitsunobu reaction (Liav and Goren, 1986), or voluminous acylating agents in presence of basic catalysts (Chauvin et al, 1993). The main drawbacks associated with these processes are the need to synthesize special electrophiles and/or the low yields obtained.…”

Section: Introductionmentioning

confidence: 99%