Shvets V I
Lomonosov Institute of Fine Chemical Technology, Department of Biotechnology, Moscow, Russian Federation.
Chem Phys Lipids. 1995 Jun 19;76(2):225-40. doi: 10.1016/0009-3084(95)02446-p.
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.
含有手性甘露糖基肌醇的鞘磷脂是由D-赤型神经酰胺和旋光性甘露糖基-肌醇通过亚磷酸三酯偶联法合成的。外消旋3,4,5,6-四-O-苄基-肌醇通过非对映体薄荷氧基乙酸酯实现对映体的拆分。碘鎓离子促进的糖基化反应已用于制备手性甘露糖基-肌醇。双（二异丙基氨基）-2-氰基乙基膦已用于在D-赤型-3-O-苯甲酰神经酰胺的伯羟基官能团与旋光性且部分苄基化的1-O-（2-O-α-D-甘露吡喃糖基）-D-肌醇的仲羟基之间引入磷酸二酯键。
