(4R)-3-[(2R,3R)-3-hydroxy-5-phenyl-2-(phenylmethoxy)pentanoyl]-4-benzyl-1,3-oxazolidin-2-one | 862423-77-6

• 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: (4R)-3-[(2R,3R)-3-hydroxy-5-phenyl-2-(phenylmethoxy)pentanoyl]-4-benzyl-1,3-oxazolidin-2-one
• 英文别名: (4R)-4-benzyl-3-[(2R,3R)-3-hydroxy-5-phenyl-2-phenylmethoxypentanoyl]-1,3-oxazolidin-2-one
• CAS: 862423-77-6
• 化学式: C₂₈H₂₉NO₅
• 分子量: 459.542
• InChiKey: OADAFFZWKCGWJZ-TWJOJJKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R)-3-[(2R,3R)-3-hydroxy-5-phenyl-2-(phenylmethoxy)pentanoyl]-4-benzyl-1,3-oxazolidin-2-one 在 lithium aluminium tetrahydride 、 camphor-10-sulfonic acid 、 水 作用下， 以 乙醇 为溶剂， 生成 (4R,5S)-5-Benzyloxy-2,2-dimethyl-4-phenethyl-[1,3]dioxane
  参考文献：
  名称：

  Complex Aldol Reactions for the Construction of Dense Polyol Stereoarrays:  Synthesis of the C₃₃−C₃₆ Region of Aflastatin A

  摘要：

  Facial selectivity in the addition of boron enolates of alpha-oxygenated ketones to anti-disposed alpha,beta-bisalkoxy aldehydes is controlled by the aldehyde vicinal diol protecting group. Protection of the diol as an acetonide results in the exclusive formation of the anti-syn-anti stereoarray found in the C-33-C-36 region of aflastatin A.

  DOI：

  10.1021/ol051226f
• 作为产物：
  描述：

  苯丙醛 、 (4R)-3-[2-(Phenylmethoxy)acetyl]-4-(phenylmethyl)oxazolidin-2-one 在 tin(II) trifluoromethanesulfonate 、 三乙胺 、 四甲基乙二胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以58%的产率得到(4R)-3-[(2R,3R)-3-hydroxy-5-phenyl-2-(phenylmethoxy)pentanoyl]-4-benzyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Complex Aldol Reactions for the Construction of Dense Polyol Stereoarrays:  Synthesis of the C₃₃−C₃₆ Region of Aflastatin A

  摘要：

  Facial selectivity in the addition of boron enolates of alpha-oxygenated ketones to anti-disposed alpha,beta-bisalkoxy aldehydes is controlled by the aldehyde vicinal diol protecting group. Protection of the diol as an acetonide results in the exclusive formation of the anti-syn-anti stereoarray found in the C-33-C-36 region of aflastatin A.

  DOI：

  10.1021/ol051226f

文献信息

• Complex Aldol Reactions for the Construction of Dense Polyol Stereoarrays:  Synthesis of the C₃₃−C₃₆ Region of Aflastatin A
  作者：David A. Evans、Frank Glorius、Jason D. Burch

  DOI：10.1021/ol051226f

  日期：2005.7.1

  Facial selectivity in the addition of boron enolates of alpha-oxygenated ketones to anti-disposed alpha,beta-bisalkoxy aldehydes is controlled by the aldehyde vicinal diol protecting group. Protection of the diol as an acetonide results in the exclusive formation of the anti-syn-anti stereoarray found in the C-33-C-36 region of aflastatin A.