ethyl 3,4,6-tri-O-benzoyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxy)carbonylamino-β-D-glucopyranoside | 1233488-70-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3,4,6-tri-O-benzoyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxy)carbonylamino-β-D-glucopyranoside
• 英文别名: TrocNH(-2d)[Bz(-3)][Bz(-4)][Bz(-6)]Glc(b)-SEt；[(2R,3S,4R,5R,6S)-3,4-dibenzoyloxy-6-ethylsulfanyl-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]methyl benzoate
• CAS: 1233488-70-4
• 化学式: C₃₂H₃₀Cl₃NO₉S
• 分子量: 711.017
• InChiKey: BZWGTUUPBSMURY-JHBWFYOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  152
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 、 ethyl 3,4,6-tri-O-benzoyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxy)carbonylamino-β-D-glucopyranoside 在 三氟甲磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.08h， 以98%的产率得到methyl O-(3,4,6-tri-O-benzoyl-2-deoxy-2-(2,2,2-trichloroethoxy)carbonylamino-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Comparison of the Armed/Disarmed Building Blocks of the d-Gluco and d-Glucosamino Series in the Context of Chemoselective Oligosaccharide Synthesis

  摘要：

  A very elegant Fraser-Reid armed-disarmed approach recently expanded to the building blocks of the superarmed and superdisarmed series shows very high utility in chemoselective oligosaccharide synthesis. Although a number of studies dedicated to the chemoselective activation of 2-amino-2-deoxysugars have emerged, little remains known about how the reactivity of the armed/disarmed building blocks of the neutral sugars directly compares to that of their 2-aminosugar counterparts. A preliminary study of this comparative reactivity is presented.

  DOI：

  10.1021/ol101089u
• 作为产物：
  描述：

  苯甲酰氯 、 ethyl 2-deoxy-<<(2,2,2-trichloroethoxy)carbonyl>amino>-1-thio-β-D-glucopyranoside 在 吡啶 作用下， 以67%的产率得到ethyl 3,4,6-tri-O-benzoyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxy)carbonylamino-β-D-glucopyranoside
  参考文献：
  名称：

  Comparison of the Armed/Disarmed Building Blocks of the d-Gluco and d-Glucosamino Series in the Context of Chemoselective Oligosaccharide Synthesis

  摘要：

  A very elegant Fraser-Reid armed-disarmed approach recently expanded to the building blocks of the superarmed and superdisarmed series shows very high utility in chemoselective oligosaccharide synthesis. Although a number of studies dedicated to the chemoselective activation of 2-amino-2-deoxysugars have emerged, little remains known about how the reactivity of the armed/disarmed building blocks of the neutral sugars directly compares to that of their 2-aminosugar counterparts. A preliminary study of this comparative reactivity is presented.

  DOI：

  10.1021/ol101089u

文献信息

• Comparison of the Armed/Disarmed Building Blocks of the <scp>d</scp>-Gluco and <scp>d</scp>-Glucosamino Series in the Context of Chemoselective Oligosaccharide Synthesis
  作者：Teerada Kamkhachorn、Archana R. Parameswar、Alexei V. Demchenko

  DOI：10.1021/ol101089u

  日期：2010.7.2

  A very elegant Fraser-Reid armed-disarmed approach recently expanded to the building blocks of the superarmed and superdisarmed series shows very high utility in chemoselective oligosaccharide synthesis. Although a number of studies dedicated to the chemoselective activation of 2-amino-2-deoxysugars have emerged, little remains known about how the reactivity of the armed/disarmed building blocks of the neutral sugars directly compares to that of their 2-aminosugar counterparts. A preliminary study of this comparative reactivity is presented.