Bz(-4)Oli(a1-3)[Bz(-4)]a-Oli1Me | 381727-51-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Bz(-4)Oli(a1-3)[Bz(-4)]a-Oli1Me
• 英文别名: [(2R,3S,4R,6R)-6-[(2R,3R,4R,6S)-3-benzoyloxy-6-methoxy-2-methyloxan-4-yl]oxy-4-hydroxy-2-methyloxan-3-yl] benzoate
• CAS: 381727-51-1
• 化学式: C₂₇H₃₂O₉
• 分子量: 500.546
• InChiKey: YWURRWRXTLGLMD-MVPHRSCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-O-acetyl-4-O-benzoyl-β-L-rhodinopyranose 、 Bz(-4)Oli(a1-3)[Bz(-4)]a-Oli1Me 在 polystyrene-bound silyl triflate 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以43.7%的产率得到Bz(-4)L-Rho(a1-3)[Bz(-4)]Oli(a1-3)[Bz(-4)]a-Oli1Me
  参考文献：
  名称：

  The First Polymer-Assisted Solution-Phase Synthesis of Deoxyglycosides

  摘要：

  [GRAPHICS]A glycosylation protocol for the synthesis of 2-deoxyglycosides has been developed which is based on the use of polymer-bound reagents. Glycals are transformed into 2-iodoglycosyl acetates using polymer-bound bis(acetoxy)iodate(1) complex (1). Activation of the anomeric center is achieved by employing polymer-bound silyl triflate (2). In the presence of different glycosyl acceptors, 2-deoxy-2-iodoglycosides are generated in very good yields. Furthermore, it is shown that this method can be embedded in multistep sequences toward glycosylated testosterone and rhodinosyl-olivosyl-olivoside.

  DOI：

  10.1021/ol016545v
• 作为产物：
  描述：

  [(2R,3R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-2-methyl-3,4-dihydro-2H-pyran-3-yl] benzoate 在 偶氮二异丁腈 、 polystyrene-bound silyl triflate 、 三正丁基氢锡 、 氟化氢吡啶 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 82.78h， 生成 Bz(-4)Oli(a1-3)[Bz(-4)]a-Oli1Me
  参考文献：
  名称：

  The First Polymer-Assisted Solution-Phase Synthesis of Deoxyglycosides

  摘要：

  [GRAPHICS]A glycosylation protocol for the synthesis of 2-deoxyglycosides has been developed which is based on the use of polymer-bound reagents. Glycals are transformed into 2-iodoglycosyl acetates using polymer-bound bis(acetoxy)iodate(1) complex (1). Activation of the anomeric center is achieved by employing polymer-bound silyl triflate (2). In the presence of different glycosyl acceptors, 2-deoxy-2-iodoglycosides are generated in very good yields. Furthermore, it is shown that this method can be embedded in multistep sequences toward glycosylated testosterone and rhodinosyl-olivosyl-olivoside.

  DOI：

  10.1021/ol016545v

文献信息

• The First Polymer-Assisted Solution-Phase Synthesis of Deoxyglycosides
  作者：Andreas Kirschning、Martin Jesberger、Andreas Schönberger

  DOI：10.1021/ol016545v

  日期：2001.11.1

  [GRAPHICS]A glycosylation protocol for the synthesis of 2-deoxyglycosides has been developed which is based on the use of polymer-bound reagents. Glycals are transformed into 2-iodoglycosyl acetates using polymer-bound bis(acetoxy)iodate(1) complex (1). Activation of the anomeric center is achieved by employing polymer-bound silyl triflate (2). In the presence of different glycosyl acceptors, 2-deoxy-2-iodoglycosides are generated in very good yields. Furthermore, it is shown that this method can be embedded in multistep sequences toward glycosylated testosterone and rhodinosyl-olivosyl-olivoside.