Synthesis of L-glucurone. Conversion of D-glucose into L-glucose
Synthesis of L-glucurone. Conversion of D-glucose into L-glucose
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L-葡萄糖醛酸的合成。
DOI：
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发表时间：
1969
期刊：
影响因子：
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通讯作者：
W. Sowa
中科院分区：
文献类型：
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作者：
W. Sowa
L-葡糖醛酮（2）可通过用摩尔当量的高碘酸处理D-甘油-D-古洛-庚内酯（1）以小规模制备;薄层色谱法用于分离。在较大规模上，从3，5; 6，7-二-O-异亚丙基-D-甘油基-D-古洛-庚内酯（4）经两步得到纯的结晶L-葡萄糖醛酮，产率超过80%，这两步包括用高碘酸同时水解和氧化4，然后用三氟乙酸处理中间氧化产物。以L-葡萄糖醛酮为原料，经硼氢化物还原和1，2-O-异丙叉衍生物水解制备L-葡萄糖。由于1衍生自D-葡萄糖，这一系列反应的结果是D-葡萄糖转化为其对映体L-葡萄糖。
L-Glucurone (2) was readily prepared on a small scale by treatment of D-glycero-D-gulo-heptono-lactone (1) with a molar equivalent of periodic acid; thin–layer chromatography was used for its isolation. On a larger scale pure crystalline L-glucurone was obtained in over 80% yield from 3,5;6,7-di-O-isopropylidene-D-glycero-D-gulo-heptonolactone (4) in two steps consisting of concomitant hydrolysis and oxidation of 4 with periodic acid followed by treatment of the intermediate oxidation product with trifluoroacetic acid. L-Glucose was prepared from L-glucurone by borohydride reduction and hydrolysis of the 1,2-O-isopropylidene derivative. Since 1 was derived from D-glucose, the result of this series of reactions was the conversion of D-glucose into its enantiomer L-glucose.