benzyl N-[(1S)-1-[(4R,5R)-2-oxo-5-propan-2-yl-1,3,2-dioxathiolan-4-yl]-2-phenylethyl]carbamate | 1055036-07-1

• 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)-2-oxo-5-propan-2-yl-1,3,2-dioxathiolan-4-yl]-2-phenylethyl]carbamate
• CAS: 1055036-07-1
• 化学式: C₂₁H₂₅NO₅S
• 分子量: 403.499
• InChiKey: BYEGOZTWWAWKGX-OJDTXMBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  93.1
• 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)-2-oxo-5-propan-2-yl-1,3,2-dioxathiolan-4-yl]-2-phenylethyl]carbamate 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 4.0h， 生成 N-苄基乙酰胺
  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：

  benzyl N-[(2S,3R,4R)-3,4-dihydroxy-5-methyl-1-phenylhexan-2-yl]carbamate 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 benzyl N-[(1S)-1-[(4R,5R)-2-oxo-5-propan-2-yl-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).