Di-tert.-butyl 2-[4-(2-tetrahydropyranyloxy)nonyl]-2-(6-ethoxycarbonylhexyl)malonate → 8-Carbamoyl-12-(R)-hydroxyheptadecanoic Acid

Participants

Reaction Steps

The synthesis of this compound is carried out exactly according to the procedure described for the 12-(S) compound of Example 13 except that in Step B, the (4S)-1-methylsulfonyloxy-4-(2-tetrahydropyranyloxy)-nonane is replaced by an equimolar amount of (4R)-1-methylsulfonyloxy-4-(2-tetrahydropyranyloxy)nonane (Example I, Step 7). The product of Step B is thus di-tert.-butyl 2-[4-(2-tetrahydropyranyloxy)nonyl]-2-(6-ethoxycarbonylhexyl)malonate. Subsequent steps yield: di-tert.-butyl 2-(4-(R)-hydroxynonyl)-2-(6ethoxycarbonylhexyl)malonate (B-1); di-tert.-butyl 2 -(4-(R)-acetoxynonyl)-2-(6-ethoxycarbonylhexyl)malonate (B-2); ethyl 8-carboxy-12-(R)-acetoxyheptadecanoate (C); ethyl 8-chlorocarbonyl-12-(R)-acetoxyheptadecanoate (D); ethyl 8-carbamoyl-12-(R)-acetoxyheptadecanoate (E); and 8-carbamoyl-12-(R)-hydroxheptadecanoic acid (F).

Provenance & Evidence