1-(acetylamino)-1-deoxy-D-arabinitol | 92283-19-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(acetylamino)-1-deoxy-D-arabinitol
• 英文别名: N-[(2R,3S,4R)-2,3,4,5-tetrahydroxypentyl]acetamide
• CAS: 92283-19-7
• 化学式: C₇H₁₅NO₅
• 分子量: 193.2
• InChiKey: WGZUILJVFZKRLL-QYNIQEEDSA-N

物化性质

• 熔点：
  142-143 °C(Solv: methanol (67-56-1))
• 沸点：
  572.7±50.0 °C(Predicted)
• 密度：
  1.368±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-乙酰氨基葡萄糖 在 Rh[1,3-bis(diphenylphosphino)propane]2Cl 作用下， 以 二乙二醇二甲醚 、 N,N-二甲基乙酰胺 为溶剂， 反应 16.0h， 以42%的产率得到1-(acetylamino)-1-deoxy-D-arabinitol
  参考文献：
  名称：

  Rhodium-Catalyzed Decarbonylation of Aldoses

  摘要：

  [Graphics]A catalytic procedure is described for decarbonylation of unprotected aldoses to afford alditols with one less carbon atom. The reaction is performed with the rhodium complex Rh(dPPP)(2)Cl in a refluxing diglyme-DMA solution. A slightly improved catalyst turnover is observed when a catalytic amount of pyridine is added. Under these conditions most hexoses and pentoses undergo decarbonylation into the corresponding pentitols and tetrols in isolated yields around 70%. The reaction has been applied as the key transformation in a five-step synthesis of L-threose from D-glucose.

  DOI：

  10.1021/jo7017729

文献信息

• Decarbonylation of unprotected aldose sugars by chlorotris(triphenylphosphine)rhodium(I). A new descent of series approach to alditols, deoxyalditols, and glycosylalditols
  作者：Mark A. Andrews、George L. Gould、Stephen A. Klaeren

  DOI：10.1021/jo00283a017

  日期：1989.10
• Rhodium-Catalyzed Decarbonylation of Aldoses
  作者：Rune Nygaard Monrad、Robert Madsen

  DOI：10.1021/jo7017729

  日期：2007.12.1

  [Graphics]A catalytic procedure is described for decarbonylation of unprotected aldoses to afford alditols with one less carbon atom. The reaction is performed with the rhodium complex Rh(dPPP)(2)Cl in a refluxing diglyme-DMA solution. A slightly improved catalyst turnover is observed when a catalytic amount of pyridine is added. Under these conditions most hexoses and pentoses undergo decarbonylation into the corresponding pentitols and tetrols in isolated yields around 70%. The reaction has been applied as the key transformation in a five-step synthesis of L-threose from D-glucose.