The synthesis of 1-O-(2-N-stearoyl-D-erythro-sphinganine-1-phosphoryl)-2-O- (alpha-D-mannopyranosyl-D-myo-inositol: a fragment of the naturally occurring inositol-containing glycophosphosphingolipids.
Chiral mannosylinositol containing sphingophospholipid was synthesized from D-erythro ceramide and optically active mannosyl-myo-inositol with the use of phosphite triester coupling procedure. The optical resolution of racemic 3,4,5,6-tetra-O-benzyl-myo-inositol to enantiomers was accomplished via diastereomeric menthoxyacetic esters. Iodonium ion-promoted glycosylation has been used for the preparation of chiral mannosyl-myo-inositol. Bis(diisopropylamino)-2-cyanoethylphosphine has been applied to the introduction of the phosphodiester bond between the primary hydroxyl function of D-erythro-3-O-benzoylceramide and the secondary hydroxyl group of optically active and partially benzylated 1-O-(2-O-alpha-D-mannopyranosyl)- D-myo-inositol.
Zamyatina AYu
Lomonosov Institute of Fine Chemical Technology, Department of Biotechnology, Moscow, Russian Federation.
Shvets
V I
VI
D006028:Glycosphingolipids / Q000138:chemical synthesis* / Q000737:chemistry*; D006031:Glycosylation; D007295:Inositol Phosphates / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D017905:Phosphites / Q000737:chemistry; D013237:Stereoisomerism
C094994:1-O-(2-N-stearoylsphinganine-1-phosphoryl)-2-O-(mannopyranosyl)inositol; D006028:Glycosphingolipids; D007295:Inositol Phosphates; D017905:Phosphites