1-(4-(Benzyloxy)-3,5-dimethoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol was synthesized from 1-(4-hydroxy-3,5-dimethoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol (Compound 0193) by debenzylation reaction. The preparation of this compound followed the methods reported in the literature (Pardini, V.L., Smith, C.Z., Utley, J.H.P., Vargas, R.R., Viertler, H. J. Org. Chem. 1991, 56, 7305).
* 1H NMR (300 MHz, CDCl3) δ: 7.14-6.90 (m, 4H), 6.68 (s, 2H, minor diastereoisomer), 6.62 (s, 2H, major diastereoisomer), 5.55 (s, 1H, minor diastereoisomer, -OH), 5.52 (s, 1H, major diastereoisomer, -OH), 4.95 (m, 1H), 4.14 (m, 1H, major diastereoisomer), 4.00 (m, 1H, minor diastereoisomer), 3.91 (s, 3H, minor diastereoisomer), 3.89 (s, 3H, major diastereoisomer), 3.88 (s, 6H, minor diastereoisomer), 3.86 (s, 6H, major diastereoisomer), 3.70-3.62 (m, 1H, major diastereoisomer). 3.70-3.62 (m, 1H, major diastereoisomer), 3.55-3.53 (m, 1H, minor diastereoisomer), 2.74 (bs, 1H).
13C NMR (75 MHz, CDCl3) Major diastereoisomers: δ 151.85, 147.32, 134.37, 131.19, 124.50, 121.89, 121.41, 112.41, 103.91, 102.9, 87.66, 73.14, 61.01, 56.58, 56.12; minor diastereoisomers: δ 151.6, 147.10, 134.71, 130.86, 124.56, 121.95, 121.31, 112.41, 103.90, 102.91, 89.74, 74.47, 61.16, 56.58, 56.14.
HRMS (EI) C18H22O7NH4 [M + NH4]+ Calculated value 368.1709, measured value 368.1704.
