(2S,3S,2'S)-3-([1,3]dioxolan-2-yl)-3'-methyl-3,4-dihydro-2H,2'H-[2,2']bifuranyl-5,5'-dione | 1426678-59-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (2S,3S,2'S)-3-([1,3]dioxolan-2-yl)-3'-methyl-3,4-dihydro-2H,2'H-[2,2']bifuranyl-5,5'-dione
• 英文别名: (2S)-2-[(2S,3S)-3-(1,3-dioxolan-2-yl)-5-oxooxolan-2-yl]-3-methyl-2H-furan-5-one
• CAS: 1426678-59-2
• 化学式: C₁₂H₁₄O₆
• 分子量: 254.24
• InChiKey: DPXKLXAGQZRENM-SWPVVBRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S,2'S)-3-([1,3]dioxolan-2-yl)-3'-methyl-3,4-dihydro-2H,2'H-[2,2']bifuranyl-5,5'-dione 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以50%的产率得到
  参考文献：
  名称：

  Diastereoselective Synthesis of Enantiopure γ-Butenolide-butyrolactones towards Pseudopterogorgia Lactone Furanocembranoid Substructures

  摘要：

  A diastereoselective methodology for preparing trans-gamma-lactone-gamma-butenolides through vinylogous aldol additions of siloxy-furanes to enantiopure cyclopropylcarbaldehyde followed by a tin-catalyzed retroaldol-lactonization cascade is reported. This synthetic approach is applied to a short synthesis of an exo-trienol furan lactone substructure relevant to bielschowskysin and other related coral diterpenoid natural products.

  DOI：

  10.1055/s-0032-1317555
• 作为产物：
  描述：

  (1R,2R,3R)-(+)-oxalic acid 2-ethoxycarbonyl-3-formylcyclopropyl ester methyl ester 在 1,3-dichloro-1,1,3,3-tetrabutylstannoxane 、 三氟化硼乙醚 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 28.5h， 生成 (2S,3S,2'S)-3-([1,3]dioxolan-2-yl)-3'-methyl-3,4-dihydro-2H,2'H-[2,2']bifuranyl-5,5'-dione
  参考文献：
  名称：

  Diastereoselective Synthesis of Enantiopure γ-Butenolide-butyrolactones towards Pseudopterogorgia Lactone Furanocembranoid Substructures

  摘要：

  A diastereoselective methodology for preparing trans-gamma-lactone-gamma-butenolides through vinylogous aldol additions of siloxy-furanes to enantiopure cyclopropylcarbaldehyde followed by a tin-catalyzed retroaldol-lactonization cascade is reported. This synthetic approach is applied to a short synthesis of an exo-trienol furan lactone substructure relevant to bielschowskysin and other related coral diterpenoid natural products.

  DOI：

  10.1055/s-0032-1317555

文献信息

• Diastereoselective Synthesis of Enantiopure γ-Butenolide-butyrolactones towards Pseudopterogorgia Lactone Furanocembranoid Substructures
  作者：Oliver Reiser、Allan Macabeo、Christian Lehmann

  DOI：10.1055/s-0032-1317555

  日期：——

  A diastereoselective methodology for preparing trans-gamma-lactone-gamma-butenolides through vinylogous aldol additions of siloxy-furanes to enantiopure cyclopropylcarbaldehyde followed by a tin-catalyzed retroaldol-lactonization cascade is reported. This synthetic approach is applied to a short synthesis of an exo-trienol furan lactone substructure relevant to bielschowskysin and other related coral diterpenoid natural products.