2,2-dimethyl-5-phenylmethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]dioxole | 245441-89-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dimethyl-5-phenylmethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]dioxole
• 英文别名: (3aR,5R,6aR)-5-benzyl-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 245441-89-8
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: WWCWPEWSZOPPER-JHJVBQTASA-N

物化性质

• 沸点：
  314.3±22.0 °C(predicted)
• 密度：
  1.101±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-5-phenylmethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]dioxole 在 硫酸 、 溶剂黄146 、 silver carbonate 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 9.0h， 生成 (+)-harzialactone A
  参考文献：
  名称：

  Synthesis of harzialactone A and its isomers from d-glucose and assignment of absolute stereochemistry

  摘要：

  The synthesis of the marine metabolite (3R,5R)-harzialactone A 1 from D-glucose is described. Syntheses of all the isomers (3S,5R)-2, (3R,5S)-3 and (3S,5S)-4 of 1 are also described and the absolute stereochemistry for the natural product 1 is assigned unambiguously. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00389-x
• 作为产物：
  描述：

  1,2-O-异亚丙基-D-呋喃葡萄糖 在 sodium periodate 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 17.0h， 生成 2,2-dimethyl-5-phenylmethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]dioxole
  参考文献：
  名称：

  A concise synthesis of harzialactone A from d-glucose and revision of absolute stereochemistry

  摘要：

  Synthesis of 2 by a chiron approach is described starting from monoacetone-D-glucose 4. Absolute stereochemistry of natural harzialactone A 1 (2S,4S) is revised to 2 (2R,4R). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00245-1

文献信息

• A concise synthesis of harzialactone A from d-glucose and revision of absolute stereochemistry
  作者：Hari Babu Mereyala、Rajendrakumar Reddy Gadikota

  DOI：10.1016/s0957-4166(99)00245-1

  日期：1999.6

  Synthesis of 2 by a chiron approach is described starting from monoacetone-D-glucose 4. Absolute stereochemistry of natural harzialactone A 1 (2S,4S) is revised to 2 (2R,4R). (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of harzialactone A and its isomers from d-glucose and assignment of absolute stereochemistry
  作者：Hari Babu Mereyala、Maju Joe、Rajendrakumar Reddy Gadikota

  DOI：10.1016/s0957-4166(00)00389-x

  日期：2000.10

  The synthesis of the marine metabolite (3R,5R)-harzialactone A 1 from D-glucose is described. Syntheses of all the isomers (3S,5R)-2, (3R,5S)-3 and (3S,5S)-4 of 1 are also described and the absolute stereochemistry for the natural product 1 is assigned unambiguously. (C) 2000 Elsevier Science Ltd. All rights reserved.