methyl (ethyl 2-O-benzoyl-3-O-benzyl-4-levulinoyl-1-thio-β-L-idopyranosyl) uronate | 1229593-67-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (ethyl 2-O-benzoyl-3-O-benzyl-4-levulinoyl-1-thio-β-L-idopyranosyl) uronate
• 英文别名: methyl (2R,3S,4S,5R,6R)-5-benzoyloxy-6-ethylsulfanyl-3-(4-oxopentanoyloxy)-4-phenylmethoxyoxane-2-carboxylate
• CAS: 1229593-67-2
• 化学式: C₂₈H₃₂O₉S
• 分子量: 544.623
• InChiKey: HNQOYUUZVBXILD-VIIRTJBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  methyl (ethyl 3-O-benzyl-4-levulinoyl-1-thio-β-L-idopyranosyl) uronate 、 苯甲酰氯 在 吡啶 作用下， 反应 1.0h， 以92%的产率得到methyl (ethyl 2-O-benzoyl-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

文献信息

• De novo synthesis of differentially protected l-iduronic acid glycosylating agents
  作者：Pascal Bindschädler、Alexander Adibekian、Dan Grünstein、Peter H. Seeberger

  DOI：10.1016/j.carres.2010.02.004

  日期：2010.5

  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.