acetyl 4-O-benzoyl-3-O-tert-butyldimethylsilyl-2,6-dideoxy-2-iodo-α-D-manno-hexopyranose | 381727-32-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: acetyl 4-O-benzoyl-3-O-tert-butyldimethylsilyl-2,6-dideoxy-2-iodo-α-D-manno-hexopyranose
• 英文别名: [(2R,3R,4S,5S,6R)-6-acetyloxy-4-[tert-butyl(dimethyl)silyl]oxy-5-iodo-2-methyloxan-3-yl] benzoate
• CAS: 381727-32-8
• 化学式: C₂₁H₃₁IO₆Si
• 分子量: 534.464
• InChiKey: QNCXEMZIJZKUSC-QTUIHCGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  acetyl 4-O-benzoyl-3-O-tert-butyldimethylsilyl-2,6-dideoxy-2-iodo-α-D-manno-hexopyranose 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 25.53h， 生成 TBDMS(-3)[Bz(-4)]D-Rha2I(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 、 alkaline earth salt of/the/ methylsulfuric acid 以 二氯甲烷 为溶剂， 反应 52.0h， 以62.4%的产率得到acetyl 4-O-benzoyl-3-O-tert-butyldimethylsilyl-2,6-dideoxy-2-iodo-α-D-manno-hexopyranose
  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