123499-67-2Relevant academic research and scientific papers
STUDY ON THE SELECTIVITY OF BENZOYLATION OF METAL CHELATES OF SUCROSE
Navia, Juan L.,Roberts, Richard A.,Wingard, Robert E.
, p. 465 - 480 (2007/10/02)
A study of the selectivity of metal chelate-directed benzoylation of sucrose dianion, relative to unchelated sucrose anion, was conducted as part of a study on new synthetic approaches to the high-potency sweetener sucralose.Ionic complexes of sucrose with various metal ions were prepared in DMF and the resulting complexes reacted at low temperature with benzoic anhydride.Cobalt and manganese salts directed esterification mostly to the 3'-OH on the fructosyl portion.Unchelated sucrose anion and other metals favored esterification at the 2-OH of the glucosyl portion.Migration of the benzoate ester along the glucose portion was observed in the direction O-2 to O-6 at moderate temperature, but at higher temperature transannular migration was observed from the glucose to the fructose ring.Reaction mixtures were analyzed by HPLC and monobenzoates identified by retention times relative to standards.Six of eight possible monobenzoates of sucrose were isolated from mixtures and identified by their 1H NMR spectra.
Enzymatic Synthesis of Various 1'-O-Sucrose and 1-O-Fructose Esters
Carrea, Giacomo,Riva, Sergio,Secundo, Francesco,Danieli, Bruno
, p. 1057 - 1061 (2007/10/02)
A crude preparation of the proteolytic enzyme subtilisin has been used to catalyse the regioselective esterification of sucrose in anhydrous dimethylformamide.In this way 1'-O-sucrose esters bearing acyl groups of different sizes and types have been synthesized.These sucrose derivatives have been hydrolysed by yeast α-glucosidase to the corresponding 1-O-fructose esters, not easily attainable by chemical methods.
