4306-35-8Relevant articles and documents
Functional importance of the sugar moiety of jasmonic acid glucoside for bioactivity and target affinity
Ueda, Minoru,Yang, Gangqiang,Nukadzuka, Yuuki,Ishimaru, Yasuhiro,Tamura, Satoru,Manabe, Yoshiyuki
, p. 55 - 58 (2015/02/02)
12-O-β-d-Glucopyranosyljasmonic acid (JAG, 1) induces nyctinastic leaf-folding of Samanea saman. The SAR studies of 1 revealed the unique role of its glycone moiety. Biological activity and the target affinity of 1 were affected by the stereochemistry of the glycone moiety. JAG belongs to a unique class of ligands in which the structure of the glycone moiety is involved in the molecular recognition by the target protein. This journal is
THE SYNTHESIS OF 1,2:5,6-DI-O-ISOPROPYLIDENE-D-MANNITOL: A COMPARATIVE STUDY
Kuszmann, Janos,Tomori, Eva,Meerwald, Ingrid
, p. 87 - 100 (2007/10/02)
Three different methods of acetonation of D-mannitol using (a) acetone and zinc chloride, (b) 2,2-dimethoxypropane, 1,2-dimethoxyethane, and tin(II)chloride, and (c) 2-methoxypropane, N,N-dimethylformamide, and p-toluenesulfonic acid were studied in detail and compared, using gas-liquid chromatographic techniques.In each reaction, isomeric diacetals are formed, but method a gives the 1,2:5,6-diacetal in the highest yield (63percent).Methods b and c give a more complex mixture of acetals than proposed in the literature, and both methods are less economical than a.A new 1,2:3,6:4,5-tri-O-isopropylidene-D-mannitol could be separated, and its graded hydrolysis was compared to that of the 1,2:3,4:5,6-triacetal.
ISOPROPYLIDENATION OF D-MANNITOL UNDER NEUTRAL CONDITIONS
Chittenden, Gordon J. F.
, p. 219 - 226 (2007/10/02)
Isopropylidenation of D-mannitol (2) under neutral conditions, by treatment with 2,2-dimethoxypropane in 1,2-dimethoxyethane, is described. 1,2:5,6-Di-O-isopropylidene-D-mannitol is the main equilibrium product, which does not undergo further substitution under the conditions used. 1,2:3,4:5,6-Tri-O-isopropylidene-D-mannitol, the other major product, was shown to be derived mainly from initial 3,4-substitution of 2.The presence of a difunctional ether, of suitable geometry, is a necessary requirement for the reaction.Some mechanistic aspects of the reaction are discussed.