| 第 39 卷第 5 期 |  | Vol. 39 No. 5 | | 2009 年 10 月 | Oct 2009 |
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所屬欄目：醫藥及中間體
1-乙酰氧基-2，3，5-三-苯甲酰氧基-β-D-呋喃核糖的合成工藝改進(jìn) |
| 鄧 燕1，陶德良1，張永強1，謝維躍2
（1. 湖南工業(yè)大學(xué) 湖南省綠色包裝與生物納米技術(shù)應用重點(diǎn)實(shí)驗室，湖南 株洲，412008；2. 湖南輕工研究院，湖南 長(cháng)沙，410015） |
| 摘 要：以D-核糖為原料經(jīng)甲基化、苯甲�；�、乙�；铣闪�1-乙酰氧基-2，3，5-三-苯甲酰氧基-β-D-呋喃核糖。系統地研究了物料配比、反應時(shí)間、反應溫度對產(chǎn)品收率的影響。較佳的制備工藝為：5.0 g（0.033 mol）D-核糖溶于20 mL 鹽酸／甲醇中，于20℃下反應3 h，所得產(chǎn)物再溶于50 mL吡啶中，滴加15 mL（0.129 mol）苯甲酰氯，于10℃下反應15 h，所得產(chǎn)物溶于40 mL冰醋酸和5 mL（0.083 mol）醋酸酐中，滴加3 mL濃硫酸于10℃反應15 h，即得產(chǎn)品，總收率達74.34%（HPLC純度98.1％）。整個(gè)路線(xiàn)反應條件溫和、原料價(jià)廉易得，有利于工業(yè)化規模生產(chǎn)。用紅外光譜、質(zhì)譜以及核磁共振氫譜對產(chǎn)物進(jìn)行了表征。 |
| 關(guān)鍵詞：1-乙酰氧基-2，3，5-三-苯甲酰氧基-β-D-呋喃核糖；合成；D-核糖；改進(jìn) |
| 中圖分類(lèi)號：Q532+.4 文獻標識碼：A 文章編號：1009-9212（2009）05- 0030-04 |
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| Improved Synthesis of 1-O-Acetyl-2，3，5-tri-O-benzoyl-β-D-ribofuranose |
| DENG Yan1，TAO De-liang1，ZHANG Yong-qiang1，XIE Wei-yue2
（1. Key laboratory of green packaging and application of biological nanotechnology，Hunan university of technology，Zhuzhou 412008， China；2. Hunan Light Industry Research Institute，Changsha 410015，China） |
| Abstract：1-O-Acetyl-2，3，5-tri-O-benzoyl-beta-D-ribofuranose was synthesized by using D-ribose as the starting material through methylation，benzoylation and acetylization. Effects of the ratio of reactants，reaction time，and reaction temperature on the yield of the product were studied in detail. The optimal reaction conditions were obtained as follows：5.0 g（0.033 mol） D-ribose was dissolved in 20 mL HCl／MeOH，followed by stirring the solution at 20℃ for 3 h. The reaction product was dissolved in 50 mL pyridine，then 15 mL（0.129 mol） benzoyl chloride was added，followed by stirring the solution at 10℃ for 15 h. The product was dissolved in a mixture of 40 mL glacial acetic acid and 5 mL（0.083 mol）acetic anhydride，then 3 mL oil of vitriol was added，the solution was stirred at 10℃ for 15 h to get the final product. By means of the above process，the total yield of 1-O-acetyl-2，3，5-tri-O-benzoyl-beta-D-ribofuranose was up to 74.34%（HPLC purity：98.1％）. The feasibility for production with mild reaction conditions and cheap raw materials make it easy to produce 1-O-acetyl-2，3，5-tri-O-benzoyl-beta-D-ribofuranose in large scale. Structure of the product was identified by IR，MS and 1H NMR characterization. |
| Key words：1-O-acetyl-2，3，5-tri-O-benzoyl-β-D-ribofuranose；synthesis；D-ribose；improvement |
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基金項目： 國家自然科學(xué)基金資助項目（60571032），湖南省自然科學(xué)基金資助項目（06JJ4012），湖南省科技計劃資助項目（2007FJ4050）。
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作者簡(jiǎn)介：鄧 燕（1971-），女，工程師，博士研究生，主要從事藥物合成和生物工程研究。（E-mail：dy_dengyan@yahoo.com.cn）
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收稿日期：2009-09-25
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