| 选择性反应及其合成应用的研究--Ⅰ.高度区域及立体选择性硼氢化和1,2:5,6一二一(0-亚异丙基)-α-D-半乳-呋喃糖合成方法的改进 |
| STUDIES ON SOME SELECTIVE REACTIONS AND THEIR SYNTHETIC APPLICATIONS--I. A Highly Regio-and Stereoselective Hydrobrnboration and Improved Synthesis of 1,2:5,6-Di-O-iso-propylidene-D-Galactofuranose |
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| 摘要: 由D-葡萄糖(Ⅰ),经四步反应可得标题化合物(Ⅴ)。为了在较短的时间内制得足够量的纯净的3-脱氧1,2:5,6-二(O-亚异丙基)-α-D-赤-己-3-烯呋喃糖(Ⅳ),可将3-O-对甲苯磺酰基-1,2:5,6-二-(O-亚异丙基)-α-D-葡-呋喃糖(Ⅲ)和粉状氢氧化钾置于Kugelrohr装置中进行反应。仔细控制反应条件,化合物(Ⅳ)的产率达到72%。在硼烷-甲硫醚配合物(H3B:SMe2)与烯(Ⅳ)起硼氢化反应后,用碱性过氧化氢处理,可得产物(Ⅴ),产率76-81%。此硼氢化反应具有高度区域选择性和立体选择性。 |
| 关键词: 硼烷-甲硫醚配合物 选择性硼氢化 合成 α-D-半乳-呋喃糖 |
| 基金项目: |
| Abstract: The title compound (V) was prepared from D-glucose (I). In order to obtain pure 3-deoxy-l,2:5,6-di-O-iso-propylidene-a-D-erythro-hex-3-enofuranose (IV) in a relatively short time, the tosylate (Ⅲ), obtained from (Ⅱ), was allowed to react with powdered potassium hydroxide in the flask of a kugelrohr apparatus instead of a sublimator. Under carefully controlled conditions, a 72% yield of pure compound (IV) was obtained. After hydroboration of the resulting olefin (IV) with the borane-methyl sulfide complex (H3B:SMe2), the reaction mixture was treated with 30% H2O2 and 3M aqueous NaOH to give pure product (V) in yields of 76-81%. The hydroboration proceeded with high regio-and stereoselectivity. |
| Keywords: borane-methyl sulfide complex selective Hydroboration synthesis a-D-galactofuranose |
| 投稿时间：1985-10-29 |
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| 刘广鉴,胡良彬.选择性反应及其合成应用的研究--Ⅰ.高度区域及立体选择性硼氢化和1,2:5,6一二一(0-亚异丙基)-α-D-半乳-呋喃糖合成方法的改进[J].无机化学学报,1986,2(1):118-121. |
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