Reactivity of melezitose and raffinose under Mitsunobu reaction conditions.
The reactivity of melezitose and raffinose under Mitsunobu conditions was studied within the scope of the use of trisaccharides for the synthesis of fatty acid esters. Melezitose led to esters with preferential substitution at primary positions following the order of reactivity 6''>6>6'. Raffinose proved to be very reluctant toward ester formation in these conditions, leading mainly to the new 3'',6''-anhydroraffinose.
Besset
Céline
C
INSA-Lyon, Institut de Chimie et de Biochimie Moléculaires et Supramoléculaires, Laboratoire de Chimie Organique, Bât. Jules Verne, 20 Avenue Albert Einstein, Villeurbanne, France.
Chambert
Stéphane
S
Queneau
Yves
Y
Kerverdo
Sébastien
S
Rolland
Hervé
H
Guilbot
Jérôme
J
D004952:Esters; D005227:Fatty Acids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008956:Models, Chemical; D015394:Molecular Structure; D019308:Palmitic Acid / Q000737:chemistry; D011887:Raffinose / Q000138:chemical synthesis / Q000737:chemistry*; D014312:Trisaccharides / Q000737:chemistry*
D004952:Esters; D005227:Fatty Acids; D014312:Trisaccharides; D019308:Palmitic Acid; D011887:Raffinose; C005190:melezitose