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Synthesis of reference compound 4 and corresponding precursor 6.
Notes: Reagents and conditions: (a) HBTU, DIPEA, DMF, rt, 3 h, 79%; (b) KOH, MeOH/H2O, rt, 1 h, 55%; (c) EDC, HOBt, (R)-BoroPro-(+)-pinanediol·HCl, DCM, 0 °C to rt, 16 h, 93%; (d) NH4OAc, NaIO4, acetone, rt, 17 h, 45%; (e) hexamethylditin, Pd(PPh3)2Cl2, dioxane, rt, 3 h, 81%; (f) EDC, HOBt, (R)-BoroPro-(+)-pinanediol·HCl, DCM, 0 °C to rt, 16 h, 59%.
