methyl (ethyl 3-O-benzyl-4-levulinoyl-1-thio-β-L-idopyranosyl) uronate | 1229593-64-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (ethyl 3-O-benzyl-4-levulinoyl-1-thio-β-L-idopyranosyl) uronate
• CAS: 1229593-64-9
• 化学式: C₂₁H₂₈O₈S
• 分子量: 440.515
• InChiKey: KYDKVEKKCFDVJM-GQUPQBGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  30.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  108.36
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl (ethyl 3-O-benzyl-4-levulinoyl-1-thio-β-L-idopyranosyl) uronate 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 3.0h， 以85%的产率得到methyl (ethyl 2-O-acetyl-3-O-benzyl-4-levulinoyl-1-thio-β-L-idopyranosyl) uronate
  参考文献：
  名称：

  De novo synthesis of differentially protected l-iduronic acid glycosylating agents

  摘要：

  A divergent de novo synthesis of six differentially protected L-iduronic acid thioglycosides from a common advanced precursor is described. The key step of this synthetic sequence is the stereoselective elongation of dithioacetal protected C5-dialdehyde 11 via a highly diastereoselective MgBr(2)center dot OEt(2)-mediated cyanation. Orthogonally protected L-iduronic acid building blocks obtained by this synthesis are expected to facilitate access to differentially sulfated heparins for microarray-based structure-activity relationship studies. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.02.004
• 作为产物：
  描述：

  methyl (ethyl 2-O-allyl-3-O-benzyl-4-levulinoyl-1-thio-β-L-idopyranosyl) uronate 在 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 、 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 20.0h， 以62%的产率得到methyl (ethyl 3-O-benzyl-4-levulinoyl-1-thio-β-L-idopyranosyl) uronate
  参考文献：
  名称：

  De novo synthesis of differentially protected l-iduronic acid glycosylating agents

  摘要：

  A divergent de novo synthesis of six differentially protected L-iduronic acid thioglycosides from a common advanced precursor is described. The key step of this synthetic sequence is the stereoselective elongation of dithioacetal protected C5-dialdehyde 11 via a highly diastereoselective MgBr(2)center dot OEt(2)-mediated cyanation. Orthogonally protected L-iduronic acid building blocks obtained by this synthesis are expected to facilitate access to differentially sulfated heparins for microarray-based structure-activity relationship studies. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.02.004