Multi-step reaction with 11 steps
1.1: tetrahydrofuran; H2O / 20 h / 25 °C
2.1: acetyl chloride / CHCl3 / 12 h / 25 °C
3.1: 0.250 g / ethanol / 5 h / 60 °C
4.1: 92 percent / Dess-Martin reagent / CH2Cl2 / 2 h / 25 °C
5.1: 87 percent / acetic acid / ethanol / 12 h / 25 °C
6.1: NaH / dimethylformamide / 0.25 h / 0 °C
6.2: 39 percent / dimethylformamide / 2 h / 25 °C
7.1: NaH / dimethylformamide / 0.5 h / 0 °C
7.2: dimethylformamide / 2 h / 25 °C
8.1: 0.210 g / sodium methoxide / methanol / 1 h / 25 °C
9.1: LiOH*H2O / methanol; H2O / 24 h / 25 °C
10.1: 0.038 g / NaHCO3; EDCI / dimethylformamide / 24 h / 25 °C
11.1: 64 percent / CuCl2; phosphate buffer / tetrahydrofuran; H2O / 7 h / 0 - 25 °C / pH 7
With
lithium hydroxide; phosphate buffer; sodium methylate; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; acetyl chloride; copper dichloride;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(03)00457-7