(Z)-3-[(4R,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-N-methoxy-N-methylprop-2-enamide | 1015481-89-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-3-[(4R,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-N-methoxy-N-methylprop-2-enamide
• CAS: 1015481-89-6
• 化学式: C₂₇H₃₇NO₅Si
• 分子量: 483.68
• InChiKey: GZPFYAKYGFSURH-KQQOSTLXSA-N

物化性质

• 沸点：
  519.4±60.0 °C(predicted)
• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-3-[(4R,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-N-methoxy-N-methylprop-2-enamide 、 氯丙烯镁 以 四氢呋喃 为溶剂， 以92%的产率得到(1Z)-1-[(4R,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]hexa-1,5-dien-3-one
  参考文献：
  名称：

  Total synthesis of A-315675 based on the cascade Overman rearrangement

  摘要：

  The chiral and stereoselective total synthesis of A-315675 1, an antiinfluenza agent, is described. The vicinal diamino moiety in 1 was stereoselectively constructed by the cascade Overman rearrangement of a vicinal allylic-homoallylic diol derived from D-tartrate. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.12.080
• 作为产物：
  描述：

  (4R,5S)-trans-2,2-dimethyl-4-tert-butyldiphenylsiloxymethyl-5-formyl-1,3-dioxolane 、 (N-甲氧基-N-甲羰基甲基)磷酸二苯酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到(Z)-3-[(4R,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-N-methoxy-N-methylprop-2-enamide
  参考文献：
  名称：

  Total synthesis of A-315675 based on the cascade Overman rearrangement

  摘要：

  The chiral and stereoselective total synthesis of A-315675 1, an antiinfluenza agent, is described. The vicinal diamino moiety in 1 was stereoselectively constructed by the cascade Overman rearrangement of a vicinal allylic-homoallylic diol derived from D-tartrate. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.12.080

文献信息

• Total synthesis of A-315675 based on the cascade Overman rearrangement
  作者：Takayuki Momose、Naoto Hama、Chiharu Higashino、Hideyuki Sato、Noritaka Chida

  DOI：10.1016/j.tetlet.2007.12.080

  日期：2008.2

  The chiral and stereoselective total synthesis of A-315675 1, an antiinfluenza agent, is described. The vicinal diamino moiety in 1 was stereoselectively constructed by the cascade Overman rearrangement of a vicinal allylic-homoallylic diol derived from D-tartrate. (c) 2007 Elsevier Ltd. All rights reserved.