来苏糖及其环外烯糖的合成与反应
Synthesis and reactions of leucrose and its exocyclic glycal.
作者信息
Thiem J, Kleeberg M
机构信息
Organisch-Chemisches Institut der Westfälischen Wilhelms-Universität, Münster, F.R.G.
出版信息
Carbohydr Res. 1990 Sep 19;205:333-45. doi: 10.1016/0008-6215(90)80151-r.
5-O-alpha-D-Glucopyranosyl-beta-D-fructopyranose (leucrose, 1) was transformed into 3,4-di-O-acetyl-1-O-methanesulfonyl-5-O-(2,3,4-tri-O-acetyl-6-O-methanes ulfonyl-alpha-D-glucopyranosyl)-beta-D-fructopyranosyl bromide (3) and 1,3,4-tri-O-benzoyl-5-O-(2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl) -beta-D-fructopyranosyl bromide (8), which were converted into derivatives (8 and 9) of 2,6-anhydro-1-deoxy-5-O-alpha-D-glucopyranosyl-D-arabino-hex-1-enitol . Hydrogenation of 8 and 9 gave the corresponding anhydroalditol derivatives. N-Iodosuccinimide-mediated glycosylation of 9 with 1,2,3,4-tetra-O-acetyl-beta-D-glucopyranose gave 1,2,3,4-tetra-O-acetyl-6-O-[3,4-di-O-benzyl-1-deoxy-1-iodo-5-O-(2,3,4,6- tetra-O-benzoyl-alpha-D-glucopyranosyl)-beta-D-fructopyranosyl]- beta-D-glucopyranose (12). Some amino, acetylated, and isopropylidene derivatives of leucrose have been prepared and characterised.
5-O-α-D-吡喃葡萄糖基-β-D-吡喃果糖（异麦芽糖，1）被转化为3,4-二-O-乙酰基-1-O-甲磺酰基-5-O-(2,3,4-三-O-乙酰基-6-O-甲磺酰基-α-D-吡喃葡萄糖基)-β-D-吡喃果糖基溴（3）和1,3,4-三-O-苯甲酰基-5-O-(2,3,4,6-四-O-苯甲酰基-α-D-吡喃葡萄糖基)-β-D-吡喃果糖基溴（8），它们被转化为2,6-脱水-1-脱氧-5-O-α-D-吡喃葡萄糖基-D-阿拉伯-己-1-烯醇的衍生物（8和9）。8和9的氢化反应得到相应的脱水糖醇衍生物。9与1,2,3,4-四-O-乙酰基-β-D-吡喃葡萄糖在N-碘代琥珀酰亚胺介导的糖基化反应下生成1,2,3,4-四-O-乙酰基-6-O-[3,4-二-O-苄基-1-脱氧-1-碘代-5-O-(2,3,4,6-四-O-苯甲酰基-α-D-吡喃葡萄糖基)-β-D-吡喃果糖基]-β-D-吡喃葡萄糖（12）。已制备并表征了异麦芽糖的一些氨基、乙酰化和异亚丙基衍生物。
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