N-[(2R,3R,4R,5S,6R)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-methoxy-4,5-bis(phenoxycarbothioyloxy)oxan-3-yl]acetamide | 1011722-85-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2R,3R,4R,5S,6R)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-methoxy-4,5-bis(phenoxycarbothioyloxy)oxan-3-yl]acetamide
• CAS: 1011722-85-2
• 化学式: C₂₉H₃₉NO₈S₂Si
• 分子量: 621.848
• InChiKey: LTOUPWBVYWJLFY-ZFXZZAOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.38
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  Methyl-2-acetamido-6-O-(t-butyldimethylsilyl)-2-desoxy-β-D-glucopyranosid 、 硫代氯甲酸苯酯 在 1,2,2,6,6-五甲基哌啶 、 N-甲基咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以55%的产率得到N-[(2R,3R,4R,5S,6R)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-hydroxy-2-methoxy-4-phenoxycarbothioyloxyoxan-3-yl]acetamide
  参考文献：
  名称：

  Site-Selective Catalysis of Phenyl Thionoformate Transfer as a Tool for Regioselective Deoxygenation of Polyols

  摘要：

  [Graphics]We report the application of peptide-embedded imidazoles as catalysts for the site-selective delivery of the phenyl thionoformate unit as a prelude to deoxygenation reactions of polyols. Methodology was developed that allows for the synthesis of thiocarboryl derivatives based on a combination of additives that include N-alkylimidazoles and FeCl3 as co-catalysts. The use of this reagent combination leads to increased reaction rates and efficient yields relative to those of simple base-mediated reactions. In terms of controlling regioselectivity during the course of polyol modification, we found that histidine-containing peptides, in combination with FeCl3, could lead to modulation of the product distribution. Through screening of peptides and control of reaction conditions, products could be observed that reflected both the inherent preference of substrates and also reversal of inherent selectivity.

  DOI：

  10.1021/jo702334z

文献信息

• Site-Selective Catalysis of Phenyl Thionoformate Transfer as a Tool for Regioselective Deoxygenation of Polyols
  作者：María Sánchez-Roselló、Angela L. A. Puchlopek、Adam J. Morgan、Scott J. Miller

  DOI：10.1021/jo702334z

  日期：2008.3.1

  [Graphics]We report the application of peptide-embedded imidazoles as catalysts for the site-selective delivery of the phenyl thionoformate unit as a prelude to deoxygenation reactions of polyols. Methodology was developed that allows for the synthesis of thiocarboryl derivatives based on a combination of additives that include N-alkylimidazoles and FeCl3 as co-catalysts. The use of this reagent combination leads to increased reaction rates and efficient yields relative to those of simple base-mediated reactions. In terms of controlling regioselectivity during the course of polyol modification, we found that histidine-containing peptides, in combination with FeCl3, could lead to modulation of the product distribution. Through screening of peptides and control of reaction conditions, products could be observed that reflected both the inherent preference of substrates and also reversal of inherent selectivity.