1,4-bis(2,3:4,6-di-O-isopropylidene-α-L-sorbofuranos-1-O-yl)but-trans-2-ene | 1380432-52-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-bis(2,3:4,6-di-O-isopropylidene-α-L-sorbofuranos-1-O-yl)but-trans-2-ene
• 英文别名: (1R,2S,6S,8S)-4,4,11,11-tetramethyl-6-[[(E)-4-[[(1R,2S,6S,8S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[6.4.0.02,6]dodecan-6-yl]methoxy]but-2-enoxy]methyl]-3,5,7,10,12-pentaoxatricyclo[6.4.0.02,6]dodecane
• CAS: 1380432-52-9
• 化学式: C₂₈H₄₄O₁₂
• 分子量: 572.65
• InChiKey: OFBNNHGTYCWGOT-YLSCBPMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1,4-bis(2,3:4,6-di-O-isopropylidene-α-L-sorbofuranos-1-O-yl)but-trans-2-ene 在 水 、 碘 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以80%的产率得到1,4-bis(2,3-O-isopropylidene-α-L-sorbofuranos-1-O-yl)but-trans-2-ene
  参考文献：
  名称：

  Selective deprotection of tethered glycoderivatives with unsaturated spacer

  摘要：

  A double regioselective deprotection of symmetrical tethered isopropylidenated monosaccharides has been elaborated. This mild and simple methodology involving iodine and acetonitrile, allows breaking of dioxolane and dioxane moieties and affords new chiral structures in good yields. Spectroscopic characterization of these molecules includes FTIR, ESI-MS, H-1 and C-13 NMR, and also 2D-COSY, HMQC and HMBC measurements.

  DOI：

  10.1515/hc.2011.022
• 作为产物：
  描述：

  1,4-二溴-2-丁烯 、 双丙酮-L-山梨糖 在 potassium hydroxide 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 12.0h， 以34%的产率得到1,4-bis(2,3:4,6-di-O-isopropylidene-α-L-sorbofuranos-1-O-yl)but-trans-2-ene
  参考文献：
  名称：

  Tethered Glycoderivatives with Unsaturated Spacer: Synthesis and Characterization

  摘要：

  Williamson coupling of diisopropylidenated monosaccharides with trans-1,4-dibromo-2-butene gave five butenylene-bridged glycoderivatives. Their spectroscopic characterization includes infrared, mass, H-1 and C-13 NMR, correlation spectrometry, and heteronuclear multiple bond and quantum correlation measurements. This work is part of our effort to obtain chiral building blocks for the synthesis of bolaform and gemini-type surfactants with enhanced biodegradability and biocompatibility.

  DOI：

  10.1080/00397911.2011.561943