Sodium Hydroxide → HCID 131724834, compound

Participants

Reaction Steps

Hexanoic acid 3-(3,4,5-trihydroxy-6-phosphonooxymethyl-tetrahydro-pyran-2-yl)-propyl ester (2.1 g, 5.25 mmol) (prepared in Example 8) was dissolved in water (50 ml) and aqueous sodium hydroxide (1M, 4 eq, 12 ml) was added and stirred for 40 minutes at room temperature after which the solution was acidified (pH˜2) with Dowex 50W X8 H+ form. The solution was washed with dichloromethane (2×100 ml) and the solvent was removed. The residue was then dissolved in a minimum of water and added dropwise to a solution of sodium acetate (1.2 eq, 0.34 g) in ethanol (150 ml) and diethyl ether (50 ml). The resulting precipitate was centrifuged and the ethanol decanted off, the residue was washed with diethyl ether (2×100 ml) and dried to give phosphoric acid mono-[3,4,5-trihydroxy-6-(3-hydroxy-propyl)-tetrahydro-pyran-2-ylmethyl] ester monosodium salt (1.01 g, 63%). 1Hnmr (500 MHz, D2O): δ 1.35-1.46 (m, 2H), 1.46-1.58 (m, 1H), 1.62-1.72 (m, 1H), 3.41-3.50 (m, 3H) 3.56 (t, J=9.0 Hz, 1H), 3.65-3.70 (m, 1H), 3.71-3.79 (m, 2H), 3.83-3.96 (m, 2H); ESMS (−ve) 301 (M−H).

Provenance & Evidence