化学学报 ›› 1996, Vol. 54 ›› Issue (8): 826-832. 上一篇    

研究论文

从D-甘露糖醇合成(2S, 3R)-鞘氨醇

孙小玲;吴毓林   

  1. 中国科学院上海有机化学研究所;中国科学院生命有机化学国家重点实验室
  • 发布日期:1996-08-15

The synthesis of (2S, 3R)-sphingosine from D-mannitol

SUN XIAOLING;WU YULIN   

  • Published:1996-08-15

以D-甘露糖醇为原料, 在制得了(2E)-4, 5-氧异亚丙基戊烯酸酯(5)以后,经不对称双羟基化反应、环硫酸酯化和叠氮化钠区域选择性开环等12步反应以7.7%的总产率合成了标题化合物的2, 3-二苯甲酰产物, 由此为鞘氨醇和神经鞘脂类化合物的合成开辟了又一新的途径。

关键词: 红外分光光度法, 质谱法, 核磁共振谱法, 国家科委基金, 甘露糖醇, 鞘氨醇, 环硫酸酯

(2E)-4, 5-O-Isopropylidene-pentenylic ester (5), obtained in 3 steps from D-mannitol, was subjected to a series of reactions such as asymmetric dihydroxidation, cyclic sulfation and regioselective opening of the cyclic sulfate by NaN3 and finally was transformed into the 2, 3-dibenzoate of (2S, 3R)-sphingosine. The overall yield from D- mannitol was 7.7%. This work has opened a new route to the synthesis of sphingosine and other sphingolipids.

Key words: INFRARED SPECTROPHOTOMETRY, MASS SPECTROGRAPHY, NMR SPECTROMETRY, MANNITE (=MANNITOL)

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