SYNTHESIS OF ALKYL 2-DEOXY-α-D-GLYCOPYRANOSIDES AND THEIR 2-DEUTERIO DERIVATIVES
SYNTHESIS OF ALKYL 2-DEOXY-α-D-GLYCOPYRANOSIDES AND THEIR 2-DEUTERIO DERIVATIVES
复制标题
烷基2-脱氧-α-D-吡喃糖苷及其2-氘代衍生物的合成
DOI：
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发表时间：
1964
期刊：
影响因子：
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通讯作者：
S. Levine
中科院分区：
文献类型：
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作者：
R. Lemieux;S. Levine
相应的醇、碘、D-葡萄糖苷三乙酸酯、高氯酸银和2，4，6-三甲基吡啶(Cloudine)在干苯中的等摩尔量反应，以近乎定量的产率生成了2-脱氧-2-碘-α-D-甘露和β-D-吡喃葡萄糖苷三乙酸甲酯、环己基和叔丁基2-脱氧-2-碘-D-甘露糖苷和DGP三乙酸酯。α-D-甘露异构体在产物中的比例按叔丁基&环己基&甲基的顺序递增。在钯存在下，碘在赤道取向(β-D-葡萄糖构型)时保持构型，而在轴向取向(α-D-甘露构型)时几乎完全缺乏立体专一性。
The methyl, cyclohexyl, and t-butyl 2-deoxy-2-iodo-α-D-manno-and β-D-glucopyranoside triacetates were formed in near quantitative yield on reaction of equimolar amounts of the corresponding alcohol, iodine, D-glucal triacetate, silver perchlorate, and 2,4,6-trimethylpyridine (collidine) in dry benzene. The proportion of the α-D-manno isomer in the product increased in the order, t-butyl > cyclohexyl > methyl. Deuterolysis of the iodide in the presence of palladium proceeded with retention of configuration when the iodine was in equatorial orientation (β-D-gluco-configuration) but with near complete lack of stereospecificity when axially oriented (α-D-manmo-configuration).