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化学学报
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化学学报 ›› 2008, Vol. 66 ›› Issue (5): 587-590. 上一篇    

研究简报

孕甾-5,20-二烯-3β-醇-3-O-β-D-吡喃木糖苷的合成

张鲁中，李立奇，任小娟，谢志翔*   

  1. (兰州大学化学化工学院 功能有机分子国家重点实验室 兰州 730000)
  • 投稿日期:2007-06-22 修回日期:2007-09-22 发布日期:2008-03-14
  • 通讯作者: 谢志翔

Synthesis of β-(Pregna-5,20-diene-3β-yl)-D-xylopyranoside

ZHANG Lu-Zhong, LI Li-Qi, REN Xiao-Juan, XIE Zhi-Xiang*   

  1. (State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000)
  • Received:2007-06-22 Revised:2007-09-22 Published:2008-03-14
  • Contact: XIE Zhi－Xiang

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以妊娠双烯醇酮醋酸酯为起始原料, 经过6步反应以15.0%的总收率, 首次合成了孕甾-5,20-二烯-3β-醇-3-O-β-D-吡喃木糖苷. 关键反应为选择性还原α,β-不饱和酮, 夏皮罗反应, Koenig-Knorr 反应.

关键词: 甾体皂苷, 选择性还原α,β-不饱和酮, 夏皮罗反应, Koenig-Knorr reaction

The first synthesis of β-(pregna-5,20-diene-3β-yl)-D-xylopyranoside was achieved from 16-dehydropregnenolon-3β-yl acetate in six steps with a 15.0% overall yield. The key steps were selective reduction of α,β-unsaturated ketone, Shapiro reaction and Koenig-Knorr reactions.

Key words: steroidal saponin, selective reduction of α,β-unsaturated ketone, Shapiro reaction, Koenig- Knorr reaction