化学合成。
化学合成; 碳水化合物合成; 组织蛋白酶K抑制剂相关研究
合成路线 1（1. 合成：89711-08-0）
产率：89%
合成条件：Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0℃; for 0.50 h; Stage #2: With potassium hydrogensulfate; water In tetrahydrofuran; diethyl ether for 0.17 h;
实验步骤：将Boc-Gly-N-甲氧基-N-甲基酰胺（19）（4.37g，20mmol）在150ml无水THF中的溶液在冰水浴中在氩气下搅拌30分钟。在氩气下通过套管将LAH在乙醚（1M）（30ml，30mmol）中的溶液加入上述充分搅拌的溶液中。将所得溶液搅拌30分钟。将硫酸氢钾（4.77g，35mmol）在60ml水中的溶液逐渐加入到反应溶液中并搅拌10分钟。减压蒸发反应混合物中的有机溶剂。向含水残余物中加入另外的60ml水，然后用DCM（100ml.x.4）萃取。将合并的DCM萃取液用1M盐酸溶液（100ml.x.4），饱和碳酸氢钠溶液（100ml.x.2）和饱和氯化钠溶液（100ml）洗涤，用4g镁干燥。硫酸盐过夜，过滤。减压蒸发溶剂得到淡黄色油状物20（2.83g），其无需进一步纯化即可使用。产量：89％。 TLC Rf = 0.44（己烷-EtOAc = 1：1）。 1H-NMR（90MHz，CDCl3）δppm：9.60（s，1H），5.26（s，br，1H），4.04（d，2H，J = 5.1Hz）和1.46（s，9H） ）。
参考文献：
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合成路线 2（2. 合成：89711-08-0）
产率：69%
合成条件：With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; Inert atmosphere
实验步骤：在氩气氛下向圆底烧瓶中加入48（0.80g，10.0mmol）和IBX36（2.80g，10.0mmol）。 将DMSO（25mL）加入到混合物中，然后在室温下继续搅拌过夜。 将反应混合物用水（200mL）淬灭并减压过滤。 滤液用乙酸乙酯萃取。 将有机层干燥（Na 2 SO 4）并减压浓缩。 通过SiO 2柱色谱法（CHCl 3：EtOAc = 7：3）纯化粗残余物，得到49（69％;点亮55％37），为油状物; 1H NMR（500MHz，CDCl3）：d 9.65（2H，br s，HCO），5.16（1H，br，NH），4.06（2H，s，CH2），1.45（9H，s，C（CH3）3）。
参考文献：
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合成路线 3（3. 合成：89711-08-0）
产率：56%
合成条件：With sodium periodate In water at 20℃; for 2 h;
实验步骤：步骤2 2-氧代乙基氨基甲酸叔丁酯：将高碘酸钠（41.52g; 194mmol; 1.00当量）分批加入到溶解在水中的2,3-二羟基丙基氨基甲酸叔丁酯（37g; 194mmol; 1.00当量）中（300毫升）。 将所得溶液在环境温度下搅拌约2小时。 过滤除去固体。 用二氯甲烷标准萃取后处理，得到标题产物，为白色固体（17g;产率56％）。 1 H NMR（300MHz，CDCl 3）δ9.65（s，1H），5.26（s，1H），4.07（d，J = 4.5Hz，2H），1.46（s，9H）。
参考文献：
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