合成路线1

Swern oxidation of derivative (I) by means of oxalyl chloride and DMSO in CH2Cl2 followed by Wittig reaction with MePPh3Br and BuLi in THF yields alkene (II), which is then converted into alcohol (III) by hydroboration with 9-BBN in EtOH and oxidation with NaOH and H2O2 in THF followed by isomer separation. Benzylation of (III) by means of NaH and BnBr (IV) in DMF, followed by hydrolysis with acetyl chloride (V) in CH2Cl2/MeOH, affords derivative (VI), which is further benzylated with BnBr (IV) and NaH in DMF and then hydrolyzed with HCl in MeOH to provide diol (VII). Derivative (VII) is O-stannylated by means of Bu2SnO in refluxing toluene and selectively allylated with allyl bromide and CsF to furnish compound (VIII), which is then benzylated with BnBr (IV) and NaH in DMF to give completely protected derivative (IX). Removal of the allyl group of (IX) is then performed by catalytic treatment with RhCl(PPh3)3 and DABCO in refluxing EtOH, and subsequent hydrolysis with HCl in refluxing acetone yields inositol derivative (X). Conversion of (X) into protected phosphatidylinositol (XII) is then performed by a standard phosphitylation protocol with BnOP(N-i-Pr2)2 and diisopropylamine-tetrazole, followed by treatment with the imidazolyl derivative (XI) in the presence of tetrazole and final adjustment of the oxidation state of the P atom by means of tert-BuOOH. Finally, hydrogenolysis of the benzyl groups of compound (XII) with Pd(OH)2/C in tert-butanol gives the desired phosphate.