82305-39-3Relevant academic research and scientific papers
Chemical and Biochemical Studies on Carbohydrate Esters. XIII. Synthesis of 6-O-, 6,6'-Di-O-, and 4,6,4',6'-Tetra-O-stearoyl-α,α-trehaloses
Yoshimoto, Kimihiro,Wakamiya, Takako,Nishikawa, Yoshihiro
, p. 1169 - 1174 (2007/10/02)
2,3,2',3'-Tetra-O-benzyl-α,α-trehalose was synthesized conveniently in improved yield according to the know pathway but under modified reaction conditions: namely, α,α-trehalose was treated with α,α-dimethoxytoluene to give its 4,6:4',6'-di-O-benzylidene derivative, which was benzylated with benzyl chloride in dimethylsulfoxyde in the presence of sodium hydride, and subsequently debenzylidenated by hydrolysis with 80percent acetic acid.Selective acylation of the key intermediate by reaction with 1.4 molar equivalents of stearoyl chloride, followed by catalytic hydrogenolysis over palladium black, afforded 6-O-stearoyl-α,α-trehalose, mp 116-122 deg C, +108.2 deg (c=1.0, chloroform), and 6,6'-di-O-stearoyl-α,α-trehalose, mp 157-160 deg C, +80.8 deg (c=1.0, chloroform), in an approximate molar ratio of 1:3.8.Similarly, 4,6,4',6'-tetra -O-stearoyl-αα-trehalose, mp 95-97 deg C and 108-110 deg C (double melting point), +54.5 deg (c=1.0, chloroform), was also obtained by the use of 4 molar equivalents of acid chloride.Based on comparison of the carbon-13 nuclear magnetic resonance ((13)C NMR) spectral data and thin-layer and gas-liquid chromatographic behavior, the major components contained in the mono- and diester preparations which had been produced in our previous work by transesterification of α,α-trehalose with methyl stearate and shown to possess interesting biological activities were identified as the 6- and 6,6'-stearates, respectively.Keywords---synthesis; 6-O-stearoyl-α,α-trehalose; 6.6'-di-O-stearoyl-α,α-trehalose; 4,6,4',6',-tetra-O-stearoyl-α,α-trehalose; 4,6:4',6'-di-O-benzylidene-α,α-trehalose; 2,3,2',3'-tetra-O-benzyl-α,α-trehalose; (13)C NMR
