p-methylphenyl (2,3,4,6-tetra-O-benzyl-β-D-galactospyranosyl)-(1->4)-2,3-di-O-benzyl-6-O-triethyl-silyl-1-thio-β-D-glucopyranoside | 1206803-46-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methylphenyl (2,3,4,6-tetra-O-benzyl-β-D-galactospyranosyl)-(1->4)-2,3-di-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-4,5-bis(phenylmethoxy)-3-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]silane
• CAS: 1206803-46-4
• 化学式: C₆₇H₇₈O₁₀SSi
• 分子量: 1103.5
• InChiKey: BEBOLHRDSNYZPI-YNEVMWMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.09
• 重原子数：
  79
• 可旋转键数：
  29
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  p-methylphenyl (2,3,4,6-tetra-O-benzyl-β-D-galactospyranosyl)-(1->4)-2,3-di-O-benzyl-6-O-triethyl-silyl-1-thio-β-D-glucopyranoside 在 四丁基氟化铵 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 C₆₁H₆₄O₁₀S
  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
• 作为产物：
  描述：

  三乙基硅烷 、 p-tolyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-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80%的产率得到p-methylphenyl (2,3,4,6-tetra-O-benzyl-β-D-galactospyranosyl)-(1->4)-2,3-di-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

• 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%).