(R)-phenyl-[(2R,3R)-3-(2-phenylmethoxyethyl)oxiran-2-yl]methanol | 1138239-05-0

• 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: (R)-phenyl-[(2R,3R)-3-(2-phenylmethoxyethyl)oxiran-2-yl]methanol
• CAS: 1138239-05-0
• 化学式: C₁₈H₂₀O₃
• 分子量: 284.355
• InChiKey: QPKYMBXXYZWXIO-KURKYZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-phenyl-[(2R,3R)-3-(2-phenylmethoxyethyl)oxiran-2-yl]methanol 、 丙酮 在 三氟化硼乙醚 作用下， 反应 4.0h， 以90%的产率得到(5R)-1-O-benzyl-2-deoxy-3,4-O-(1-methylethylidene)-5-C-phenyl-D-erythro-pentitol
  参考文献：
  名称：

  First stereoselective total synthesis of Goniothalesdiol A

  摘要：

  The first total synthesis of Goniothalesdiol A, isolated from the stems of Goniothalamus amuyon (Annonaceae) is reported. The C2 stereocentre and C3/C4 syn diol were created by a Sharpless kinetic resolution followed by acetonide formation. The tetrahydropyran ring was formed and the C6 stereocentre was fixed by intramolecular oxy-Michael addition. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2009.01.050
• 作为产物：
  描述：

  (E)-1-phenylpent-2-ene-1,5-diol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 D-(-)-酒石酸二异丙酯 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以80%的产率得到(R)-phenyl-[(2R,3R)-3-(2-phenylmethoxyethyl)oxiran-2-yl]methanol
  参考文献：
  名称：

  First stereoselective total synthesis of Goniothalesdiol A

  摘要：

  The first total synthesis of Goniothalesdiol A, isolated from the stems of Goniothalamus amuyon (Annonaceae) is reported. The C2 stereocentre and C3/C4 syn diol were created by a Sharpless kinetic resolution followed by acetonide formation. The tetrahydropyran ring was formed and the C6 stereocentre was fixed by intramolecular oxy-Michael addition. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2009.01.050

文献信息

• First stereoselective total synthesis of Goniothalesdiol A
  作者：J.S. Yadav、N. Rami Reddy、V. Harikrishna、B.V. Subba Reddy

  DOI：10.1016/j.tetlet.2009.01.050

  日期：2009.3

  The first total synthesis of Goniothalesdiol A, isolated from the stems of Goniothalamus amuyon (Annonaceae) is reported. The C2 stereocentre and C3/C4 syn diol were created by a Sharpless kinetic resolution followed by acetonide formation. The tetrahydropyran ring was formed and the C6 stereocentre was fixed by intramolecular oxy-Michael addition. (C) 2009 Published by Elsevier Ltd.