1-Adamantanecarbonyl chloride → Decane

Participants

Reaction Steps

The dimethoxytrityl group of the derivatized CPG from Example 9 is removed by a treatment with 2% dichloroacetic acid followed by washing with dry acetonitrile. The CPG is washed with acetonitrile-pyridine (1:1) followed by a simultaneous treatment of the CPG with 10 to 30 equivalents of the 10-O-(dimethoxytrityl)decyl-phosphonic acid as the triethylammonium salt, 20-30 equivalents of adamantane carbonyl chloride in acetonitrile-pyridine. The CPG is then washed with acetonitrile-pyridine and then treated with diisopropyl phosphite adamantane carbonyl chloride (0.2M) to cap all unreacted hydroxyl groups. Finally, the CPG is washed with acetonitrile/pyridine 1:1 and then acetonitrile. An estimate of coupling efficiency is derived from the treatment of the CPG with dichloracetic acid in acetonitrile followed by a measurement of the absorbance of an aliquot at 498 nm. Repeating the above procedure n times will yield an oligomer with n+1 decane units and n H-phosphonate linkages. The oligomer is tethered to a LCAA CPG by a succinate group as described above.

Provenance & Evidence