2-[(R)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-nitro-ethyl]-malonic acid dimethyl ester | 501921-27-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-[(R)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-nitro-ethyl]-malonic acid dimethyl ester
• 英文别名: dimethyl 2-[(1R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-nitroethyl]propanedioate
• CAS: 501921-27-3
• 化学式: C₁₂H₁₉NO₈
• 分子量: 305.285
• InChiKey: SZHJNPRKVXRRHJ-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-[(R)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-nitro-ethyl]-malonic acid dimethyl ester 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 (3R,3AS,6AR)-六氢呋喃并[2,3-B]呋喃-3-醇
  参考文献：
  名称：

  Stereoselective and Efficient Synthesis of (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol

  摘要：

  [GRAPHICS]Two short and efficient synthesis routes have been developed for bis-THF-alcohol 2, a key building block of the investigational HIV protease inhibitor TMC114 (1). Using S-2,3-O-isopropylideneglyceraldehyde (4) as the source of chirality, both routes are based on a diastereoselective Michael addition of nitromethane to give predominantly the syn congeners 6 followed by a Nef oxidation and cyclization to afford lactone acetals 8, which are reduced and cyclized to give 2.

  DOI：

  10.1021/ol052554i
• 作为产物：
  描述：

  (3S,4R,5S)-5-[(4S)-2,2-二甲基-1,3-二氧戊环-4-基]-3,4-二羟基二氢-2(3H)-呋喃酮 在 吡啶 、 potassium metaperiodate 、 乙酸酐 、 potassium hydrogencarbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 19.5h， 生成 2-[(R)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-nitro-ethyl]-malonic acid dimethyl ester
  参考文献：
  名称：

  Stereoselective and Efficient Synthesis of (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol

  摘要：

  [GRAPHICS]Two short and efficient synthesis routes have been developed for bis-THF-alcohol 2, a key building block of the investigational HIV protease inhibitor TMC114 (1). Using S-2,3-O-isopropylideneglyceraldehyde (4) as the source of chirality, both routes are based on a diastereoselective Michael addition of nitromethane to give predominantly the syn congeners 6 followed by a Nef oxidation and cyclization to afford lactone acetals 8, which are reduced and cyclized to give 2.

  DOI：

  10.1021/ol052554i

文献信息

• Stereoselective and Efficient Synthesis of (3<i>R</i>,3a<i>S</i>,6a<i>R</i>)-Hexahydrofuro[2,3-<i>b</i>]furan-3-ol
  作者：Peter J. L. M. Quaedflieg、Bart R. R. Kesteleyn、Piet B. T. P. Wigerinck、Nicolaas M. F. Goyvaerts、Robert Jan Vijn、Constantinus S. M. Liebregts、Jaap H. M. H. Kooistra、Claudia Cusan

  DOI：10.1021/ol052554i

  日期：2005.12.1

  [GRAPHICS]Two short and efficient synthesis routes have been developed for bis-THF-alcohol 2, a key building block of the investigational HIV protease inhibitor TMC114 (1). Using S-2,3-O-isopropylideneglyceraldehyde (4) as the source of chirality, both routes are based on a diastereoselective Michael addition of nitromethane to give predominantly the syn congeners 6 followed by a Nef oxidation and cyclization to afford lactone acetals 8, which are reduced and cyclized to give 2.