Bushnev A S, Hendrickson E K, Shvets V I, Hendrickson H S
Department of Chemistry, St Olaf College, Northfield, MN.
Bioorg Med Chem. 1994 Mar;2(3):147-51. doi: 10.1016/s0968-0896(00)82010-6.
The synthesis of optically-active hexadecyl thiophosphoryl-1-D-myo-inositol 11 was accomplished from 2,3-O-(D-1',7',7'-trimethyl[2.2.1]bicyclohept-2'-ylidene)-4,5,6-O- tris(methoxymethyl)-D-myo-inositol 6 or 2,3,4,5,6-O-pentakis(methoxymethyl)-D-myo-inositol 14, using the Arbusov reaction of their dimethyl phosphite derivatives 7 and 15 with N-hexadecyl thiophthalimide 8. This product was a substrate for phosphatidylinositol-specific phospholipase C from Bacillus cereus.
光学活性的十六烷基硫代磷酰基-1-D-肌醇11是由2,3-O-(D-1',7',7'-三甲基[2.2.1]双环庚-2'-亚基)-4,5,6-O-三(甲氧基甲基)-D-肌醇6或2,3,4,5,6-O-五(甲氧基甲基)-D-肌醇14合成的,使用它们的亚磷酸二甲酯衍生物7和15与N-十六烷基硫代邻苯二甲酰亚胺8的阿尔布佐夫反应。该产物是蜡样芽孢杆菌磷脂酰肌醇特异性磷脂酶C的底物。