1,2-Dichlorobenzene → (2'S,3'R,4'S,5'S,6'R)-7-chloro-6-(4-ethylbenzyl)-2,6'-bis(hydroxymethyl)-2-methyl-3',4',5',6'-tetrahydrospiro[chroman-4,2'-pyran]-3',4',5'-triol

Participants

Reaction Steps

To a solution of 51 (13 mg, 15.5 μmol) in a mixture of MeOH (1.2 mL) and THF (0.4 mL) was added Pd(OH)2/C (15 mg) and 1,2-dichlorobenzene (20 μL). A balloon of hydrogen gas was attached for 0.5 h with vigorous stirring. LC/MS indicated that de-protection was complete. The reaction mixture was filtered through Celite, concentrated to a residue, and purified via preparatory TLC (5% MeOH in DCM) to give 52 (2.8 mg, 38%). 1H NMR (300 MHz, CD3OD) δ 7.34 (s, 1H), 7.07 (s, 4H), 6.81 (s, 1H), 3.97 (s, 2H), 3.85 (dd, J=2.1, 11.1 Hz, 1H), 3.67-3.74 (m, 3H), 3.44-3.56 (m, 3H), 3.23 (t, J=9.3 Hz, 1H), 2.58 (q, J=7.5 Hz, 2H), 2.45 (d, J=15.3 Hz, 1H), 2.16 (d, J=15.6 Hz, 1H), 1.42 (s, 3H), 1.19 (t, J=7.5 Hz, 3H). LCMS m/z 479 (M+H), 501 (M+Na).

Provenance & Evidence