Watanabe, Yutaka; Yamamoto, Takashi; Ozaki, Shoichiro published the artcile< Regiospecific Synthesis of 2,6-Di-O-(α-D-mannopyranosyl)phosphatidyl-D-myo-inositol>, SDS of cas: 112-63-0, the main research area is inositol regioselective stereoselective glycosidation; mannopyranosylphosphatidylinositol preparation.
A concise synthesis of 2,6-di-O-α-D-mannopyranosylphosphatidyl-D-myo-inositol I [R = CO(CH2)16Me] has been accomplished by completely regioselective introduction of the requisite substituents on myo-inositol. The pivotal intermediate, 1,2-O-cyclohexylidene-3,4-O-(tetraisopropyldisiloxane-1,3-diyl)-myo-inositol, was glycoylated regioselectively at the 6-position using a mannopyranosyl phosphite as the glycosyl donor. After removing the cyclohexylidene group, the resultant 1,2-diol derivative was phosphorylated by the reaction with a glycerol phosphite in the presence of pyridinium bromide perbromide to afford regioselectively 1-O-phosphate. This was then glycosylated regio- and stereoselectively at the 2-position by the phosphite approach as above. The 1,2-O-carbonyl protecting group in the glycerol moiety was removed by the reaction with the ethylmagnesium chloride without the migration of the phosphite function, and the resulting diol was acylated and finally deprotected.
Journal of Organic Chemistry published new progress about Glycosylation. 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, SDS of cas: 112-63-0.
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