anti-(4R,2'R,3'R)-3-[2'-bromo-3'-hydroxy-3'-(3,4-bis(benzyloxy)phenyl)-propionyl]-4-benzyloxazolidin-2-one | 931385-44-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: anti-(4R,2'R,3'R)-3-[2'-bromo-3'-hydroxy-3'-(3,4-bis(benzyloxy)phenyl)-propionyl]-4-benzyloxazolidin-2-one
• 英文别名: (4R)-4-benzyl-3-[(2R,3R)-3-[3,4-bis(phenylmethoxy)phenyl]-2-bromo-3-hydroxypropanoyl]-1,3-oxazolidin-2-one
• CAS: 931385-44-3
• 化学式: C₃₃H₃₀BrNO₆
• 分子量: 616.508
• InChiKey: ZAQQDYFETKPJLX-VEIFUORISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  anti-(4R,2'R,3'R)-3-[2'-bromo-3'-hydroxy-3'-(3,4-bis(benzyloxy)phenyl)-propionyl]-4-benzyloxazolidin-2-one 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以82%的产率得到(4R)-3-[(2S,3R)-2-azido-3-[3,4-bis(phenylmethoxy)phenyl]-3-hydroxypropanoyl]-4-benzyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  NaIO4-mediated asymmetric bromohydroxylation of α,β-unsaturated carboxamides with high diastereoselectivity: a short route to (−)-cytoxazone and droxidopa

  摘要：

  The NaIO4-mediated asymmetric bromohydroxylation of alpha,beta-unsaturated carboxamides was achieved using lithium bromide as the bromine source under acidic conditions at rt to afford the corresponding chiral alpha-bromo-beta-hydroxy carboxamides. Excellent yields (77-90%) and diastereoselectivities (up to 10:1) along with exclusive control over regio- as well as anti-selectivity are the main features with a good scope of substrates. The method has successfully been applied in the enantioselective syntheses of two biologically important molecules, viz (-)-cytoxazone and L-threo-DOPS (droxidopa). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.12.109
• 作为产物：
  描述：

  (4R)-4-benzyl-3-[(E)-3-[3,4-bis(phenylmethoxy)phenyl]prop-2-enoyl]-1,3-oxazolidin-2-one 在 sodium periodate 、 氢气 、 lithium bromide 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 生成 anti-(4R,2'R,3'R)-3-[2'-bromo-3'-hydroxy-3'-(3,4-bis(benzyloxy)phenyl)-propionyl]-4-benzyloxazolidin-2-one 、
  参考文献：
  名称：

  NaIO4-mediated asymmetric bromohydroxylation of α,β-unsaturated carboxamides with high diastereoselectivity: a short route to (−)-cytoxazone and droxidopa

  摘要：

  The NaIO4-mediated asymmetric bromohydroxylation of alpha,beta-unsaturated carboxamides was achieved using lithium bromide as the bromine source under acidic conditions at rt to afford the corresponding chiral alpha-bromo-beta-hydroxy carboxamides. Excellent yields (77-90%) and diastereoselectivities (up to 10:1) along with exclusive control over regio- as well as anti-selectivity are the main features with a good scope of substrates. The method has successfully been applied in the enantioselective syntheses of two biologically important molecules, viz (-)-cytoxazone and L-threo-DOPS (droxidopa). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.12.109