区域异构体α-L-阿拉伯呋喃二糖苷甲基酯的合成。
Synthesis of regioisomeric methyl alpha-L-arabinofuranobiosides.
作者信息
Kawabata Y, Kaneko S, Kusakabe I, Gama Y
机构信息
Institute of Applied Biochemistry, University of Tsukuba, Ibaraki, Japan.
出版信息
Carbohydr Res. 1995 Feb 1;267(1):39-47. doi: 10.1016/0008-6215(94)00290-v.
The three regioisomers of methyl alpha-L-arabinofuranobioside, namely methyl O-alpha-L-arabinofuranosyl-(1-->2)-alpha-L-arabinofuranoside, methyl O-alpha-L-arabinofuranosyl-(1-->3)-alpha-L-arabinofuranoside, and methyl O-alpha-L-arabinofuranosyl-(1-->5)-alpha-L-arabinofuranoside, were synthesized for use as substrates in studies of the specificity of alpha-L-arabinofuranosidase. The regiospecifically protected precursors, namely methyl 3,5-di-O-benzoyl-alpha-L-arabinofuranoside, methyl 2,5-di-O-benzyl-alpha-L-arabinofuranoside, and methyl 2,3-di-O-benzoyl-alpha-L-arabinofuranoside, were prepared from 2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl chloride (4) and methyl 5-O-trityl-alpha-L-arabinofuranoside, respectively, and glycosylated with 4 in the presence of silver trifluoromethanesulfonate and s-collidine. 1H and 13C NMR data for all compounds are presented.
合成了α-L-阿拉伯呋喃糖甲苷的三种区域异构体，即O-α-L-阿拉伯呋喃糖基-(1→2)-α-L-阿拉伯呋喃糖苷甲酯、O-α-L-阿拉伯呋喃糖基-(1→3)-α-L-阿拉伯呋喃糖苷甲酯和O-α-L-阿拉伯呋喃糖基-(1→5)-α-L-阿拉伯呋喃糖苷甲酯，用作研究α-L-阿拉伯呋喃糖苷酶特异性的底物。区域特异性保护的前体，即3,5-二-O-苯甲酰基-α-L-阿拉伯呋喃糖苷甲酯、2,5-二-O-苄基-α-L-阿拉伯呋喃糖苷甲酯和2,3-二-O-苯甲酰基-α-L-阿拉伯呋喃糖苷甲酯，分别由2,3,5-三-O-苯甲酰基-α-L-阿拉伯呋喃糖基氯(4)和5-O-三苯甲基-α-L-阿拉伯呋喃糖苷甲酯制备，并在三氟甲磺酸银和s-可力丁存在下与4进行糖基化反应。给出了所有化合物的1H和13C NMR数据。
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