Wu Y, Blackwell L F
Department of Chemistry & Biochemistry, Massey University, Palmerston North, New Zealand.
Steroids. 1993 Oct;58(10):452-6. doi: 10.1016/0039-128x(93)90001-4.
An efficient and convenient procedure for the synthesis of estriol 16- and 17-monoglucuronides from estriol is described. This is achieved by the selective protection and deprotection of the hydroxy groups in estriol, Koenigs-Knorr reactions with methyl 1-bromo-1-deoxy-2,3,4-tri-O-acetyl-alpha-D-glucopyranuronate and subsequent hydrolysis. The products have been characterized by proton nuclear magnetic resonance (1H NMR), two-dimensional 1H homonuclear shift-correlated spectra (2D-COSY) and mass spectra. The selective Koenigs-Knorr reaction of the alcoholic hydroxyl group in the presence of a phenolic hydroxyl group is also reported.
描述了一种从雌三醇合成雌三醇16 -和17 -单葡萄糖醛酸苷的高效便捷方法。这是通过对雌三醇中羟基进行选择性保护和脱保护、与1 -溴- 1 -脱氧- 2,3,4 -三- O -乙酰基-α-D-吡喃葡萄糖醛酸甲酯进行柯尼希斯-克诺尔反应以及随后的水解来实现的。产物已通过质子核磁共振（1H NMR）、二维1H同核位移相关谱（2D-COSY）和质谱进行了表征。还报道了在酚羟基存在下醇羟基的选择性柯尼希斯-克诺尔反应。
