benzyl N-[(1S)-1-[(4R,5R)-5-(2-methylpropyl)-2,2-dioxo-1,3,2-dioxathiolan-4-yl]-2-phenylethyl]carbamate | 182204-79-1

• 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: benzyl N-[(1S)-1-[(4R,5R)-5-(2-methylpropyl)-2,2-dioxo-1,3,2-dioxathiolan-4-yl]-2-phenylethyl]carbamate
• CAS: 182204-79-1
• 化学式: C₂₂H₂₇NO₆S
• 分子量: 433.525
• InChiKey: FKLIWHFNEZABFF-PWRODBHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  99.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl N-[(1S)-1-[(4R,5R)-5-(2-methylpropyl)-2,2-dioxo-1,3,2-dioxathiolan-4-yl]-2-phenylethyl]carbamate 在 palladium on activated charcoal 、 Rh/Al₂O₃ 硫酸 、 氢气 、 三乙胺 作用下， 25.0 ℃ 、344.73 kPa 条件下， 反应 18.5h， 生成 (4S,5S)-4-cyclohexylmethyl-5-<(1'R)-1'-hydroxy-3-methylbutyl>oxazolidin-2-one
  参考文献：
  名称：

  Selective Inversion of the Proximal or Distal Hydroxyl Groups in syn,syn-3-[N-(Alkoxycarbonyl)amino] 1,2-Diols via Cyclic Sulfates

  摘要：

  The formation of cyclic sulfates (4) from syn,syn-3-[N-(benzyloxycarbonyl)amino] 1,2-diols provides a common intermediate to access other diastereomers via two inversion procedures. Thermolysis of the cyclic sulfates in acetonitrile normally leads to inversion of the distal hydroxyl group to form a 1,3-oxazin-2-one (6). Catalytic hydrogenation of the cyclic sulfates under basic conditions (NEt(3)) results in inversion at the proximal hydroxyl group to form a 1,3-oxazolidin-2-one (5).

  DOI：

  10.1021/jo961060j
• 作为产物：
  描述：

  (2S,3R,4R)-2--6-methyl-1-phenylheptane-3,4-diol 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 4.08h， 生成 benzyl N-[(1S)-1-[(4R,5R)-5-(2-methylpropyl)-2,2-dioxo-1,3,2-dioxathiolan-4-yl]-2-phenylethyl]carbamate
  参考文献：
  名称：

  Selective Inversion of the Proximal or Distal Hydroxyl Groups in syn,syn-3-[N-(Alkoxycarbonyl)amino] 1,2-Diols via Cyclic Sulfates

  摘要：

  The formation of cyclic sulfates (4) from syn,syn-3-[N-(benzyloxycarbonyl)amino] 1,2-diols provides a common intermediate to access other diastereomers via two inversion procedures. Thermolysis of the cyclic sulfates in acetonitrile normally leads to inversion of the distal hydroxyl group to form a 1,3-oxazin-2-one (6). Catalytic hydrogenation of the cyclic sulfates under basic conditions (NEt(3)) results in inversion at the proximal hydroxyl group to form a 1,3-oxazolidin-2-one (5).

  DOI：

  10.1021/jo961060j

文献信息

• Selective Inversion of the Proximal or Distal Hydroxyl Groups in <i>syn,syn</i>-3-[<i>N</i>-(Alkoxycarbonyl)amino] 1,2-Diols via Cyclic Sulfates
  作者：Scott J. Kemp、Jianming Bao、Steven F. Pedersen

  DOI：10.1021/jo961060j

  日期：1996.1.1

  The formation of cyclic sulfates (4) from syn,syn-3-[N-(benzyloxycarbonyl)amino] 1,2-diols provides a common intermediate to access other diastereomers via two inversion procedures. Thermolysis of the cyclic sulfates in acetonitrile normally leads to inversion of the distal hydroxyl group to form a 1,3-oxazin-2-one (6). Catalytic hydrogenation of the cyclic sulfates under basic conditions (NEt(3)) results in inversion at the proximal hydroxyl group to form a 1,3-oxazolidin-2-one (5).