p-methylphenyl 2,3,4-tri-O-benzyl-6-O-triethyl-silyl-1-thio-β-D-glucopyranoside | 1206803-28-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methylphenyl 2,3,4-tri-O-benzyl-6-O-triethyl-silyl-1-thio-β-D-glucopyranoside
• 英文别名: triethyl-[[(2R,3R,4S,5R,6S)-6-(4-methylphenyl)sulfanyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]silane
• CAS: 1206803-28-2
• 化学式: C₄₀H₅₀O₅SSi
• 分子量: 670.986
• InChiKey: DCWDKWZUSPMRJA-DTQLOPILSA-N

物化性质

• 沸点：
  704.5±60.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.59
• 重原子数：
  47
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  p-methylphenyl 2,3,4-tri-O-benzyl-6-O-triethyl-silyl-1-thio-β-D-glucopyranoside 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 p-methylphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Co 2（CO）8 / Et 3 SiH / CO系统温和的糖类区域选择性去O-甲基化方法

  摘要：

  开发了一种利用Co 2（CO）8 / Et 3 SiH / CO系统从保护糖上裂解甲基醚的新方法。该方法在具有各种异头基团的不同受保护单糖中显示区域选择性。优先除去伯和赤道仲甲基醚。此方法已成功应用于高度甲基化的伊德拉帕林的DEF三糖链段的合成。

  DOI：

  10.1016/j.tet.2016.07.081
• 作为产物：
  描述：

  三乙基硅烷 、 p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside 在 dicobalt octacarbonyl 、 一氧化碳 作用下， 以 苯 为溶剂， 20.0~50.0 ℃ 、101.33 kPa 条件下， 反应 24.25h， 以92%的产率得到p-methylphenyl 2,3,4-tri-O-benzyl-6-O-triethyl-silyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Highly Efficient and Mild Method for Regioselective De-O-benzylation of Saccharides by Co₂(CO)₈-Et₃SiH−CO Reagent System

  摘要：

  A highly efficient and mild method for the de-O-benzylation of protected saccharides was developed by transforming terminal benzyl ethers into silyl ethers using Co-2(CO)(8)-Et3SiH under 1 atm of CO. The method was successfully used for the de-O-benzylation of perbenzylated monosaccharides with various anomeric protecting groups, as well as natural disaccharides and trisaccharides such as sucrose, raffinose, and melezitose in good yields (>80%).

  DOI：

  10.1021/ol902717y

文献信息

• A mild method for regioselective de-O-methylation of saccharides by Co2(CO)8/Et3SiH/CO system
  作者：Yue-tao Zhao、Lu-bai Huang、Qing Li、Zhong-jun Li

  DOI：10.1016/j.tet.2016.07.081

  日期：2016.9

  A new method for cleaving methyl ethers off protected saccharides using Co2(CO)8/Et3SiH/CO system was developed. The method showed regioselectivity in different protected monosaccharides with various anomeric groups. The primary and equatorial secondary methyl ethers were preferentially removed. This method was successfully applied to the synthesis of the DEF trisaccharide segment of Idraparinux, which

  开发了一种利用Co 2（CO）8 / Et 3 SiH / CO系统从保护糖上裂解甲基醚的新方法。该方法在具有各种异头基团的不同受保护单糖中显示区域选择性。优先除去伯和赤道仲甲基醚。此方法已成功应用于高度甲基化的伊德拉帕林的DEF三糖链段的合成。
• Highly Efficient and Mild Method for Regioselective De-<i>O</i>-benzylation of Saccharides by Co₂(CO)₈-Et₃SiH−CO Reagent System
  作者：Zhao-Jun Yin、Bo Wang、Yang-Bing Li、Xiang-Bao Meng、Zhong-Jun Li

  DOI：10.1021/ol902717y

  日期：2010.2.5

  A highly efficient and mild method for the de-O-benzylation of protected saccharides was developed by transforming terminal benzyl ethers into silyl ethers using Co-2(CO)(8)-Et3SiH under 1 atm of CO. The method was successfully used for the de-O-benzylation of perbenzylated monosaccharides with various anomeric protecting groups, as well as natural disaccharides and trisaccharides such as sucrose, raffinose, and melezitose in good yields (>80%).