(2R,3R,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-eth-(E)-ylidene-tetrahydro-pyran | 934367-12-1

• 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: (2R,3R,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-eth-(E)-ylidene-tetrahydro-pyran
• CAS: 934367-12-1
• 化学式: C₂₉H₃₂O₄
• 分子量: 444.571
• InChiKey: WXCPBQAMYXPYCX-MPFGFTFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.07
• 重原子数：
  33.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  双丙酮半乳糖 、 (2R,3R,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-eth-(E)-ylidene-tetrahydro-pyran 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以78%的产率得到(3aR,5R,5aS,8aS,8bR)-5-((2S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-ethyl-tetrahydro-pyran-2-yloxymethyl)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran
  参考文献：
  名称：

  Stereoselective glycosidations of olefinated sugars

  摘要：

  The glycosidation of olefinated sugars using a catalytic amount of boron trichloride or triphenylphosphine hydrobromide proceeded in a highly stereoselective fashion to give the alpha anomers with good to high yields. The use of camphorsulphonic acid also afforded high stereoselectivity but lower yields were obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02251-7
• 作为产物：
  描述：

  乙醛 、 (3,4,6-tri-O-benzyl-2-deoxy-α/β-D-galactopyranosyl)-triphenylphosphonium tetrafluoroborate 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以65%的产率得到(2R,3R,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-eth-(E)-ylidene-tetrahydro-pyran
  参考文献：
  名称：

  Stereoselective glycosidations of olefinated sugars

  摘要：

  The glycosidation of olefinated sugars using a catalytic amount of boron trichloride or triphenylphosphine hydrobromide proceeded in a highly stereoselective fashion to give the alpha anomers with good to high yields. The use of camphorsulphonic acid also afforded high stereoselectivity but lower yields were obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02251-7