5-O-allyl-1,2:3,4-di-O-isopropylidenexylitol | 118712-45-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-allyl-1,2:3,4-di-O-isopropylidenexylitol
• 英文别名: (4S,5R)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-5-(prop-2-enoxymethyl)-1,3-dioxolane
• CAS: 118712-45-1
• 化学式: C₁₄H₂₄O₅
• 分子量: 272.342
• InChiKey: BMVILZZRUNNSEG-WOPDTQHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-O-allyl-1,2:3,4-di-O-isopropylidenexylitol 在 C.I.酸性橙108 、 过氧化苯甲酰 作用下， 以 乙醇 为溶剂， 反应 3.33h， 生成 (Z)-5-O-<3'-(F-hexyl)-2'-propenyl>-1,2:3,4-di-O-isopropylidenexylitol
  参考文献：
  名称：

  Synthesis of perfluoroalkylated xylitol ethers and esters: new surfactants for biomedical uses

  摘要：

  New, well-defined surfactants and cosurfactants were synthesized with the objective of enhancing the stability of fluorocarbon emulsions destined to serve as oxygen carriers for biomedical applications. Monoperfluoroalkylated ethers of xylitol were achieved by addition of perfluoroalkyl iodide on the double bond of a protected xylitol allyl ether in a one-step addition-elimination reaction. Monoesters were obtained specifically on position 5 by treating 1,2:3,4-di-O-isopropylidenexylitol with perfluoroalkylated acid chlorides of various chain lengths in pyridine at room temperature. The products display strong surface activity and produce a remarkable synergistic stabilization of a fluorocarbon/Pluronic F-68 type emulsion. Biocompatibility data are reported, which include in vitro toxicity tests on Namalva cell cultures and hemolysis tests on human blood cells; the latter was found to decrease as the length of the F-alkyl chain increased. IV injection in mice (n = 10) showed that these products were innocuous at 400-1000 mg/kg of body weight. Preliminary exchange-perfusion experiments on rats with an emulsion containing the F-octyl xylitol ether were encouraging.

  DOI：

  10.1021/jm00166a028
• 作为产物：
  描述：

  Xylitol 在 硫酸 、 sodium hydride 、 copper(II) sulfate 作用下， 反应 63.0h， 生成 5-O-allyl-1,2:3,4-di-O-isopropylidenexylitol
  参考文献：
  名称：

  Synthesis of perfluoroalkylated xylitol ethers and esters: new surfactants for biomedical uses

  摘要：

  New, well-defined surfactants and cosurfactants were synthesized with the objective of enhancing the stability of fluorocarbon emulsions destined to serve as oxygen carriers for biomedical applications. Monoperfluoroalkylated ethers of xylitol were achieved by addition of perfluoroalkyl iodide on the double bond of a protected xylitol allyl ether in a one-step addition-elimination reaction. Monoesters were obtained specifically on position 5 by treating 1,2:3,4-di-O-isopropylidenexylitol with perfluoroalkylated acid chlorides of various chain lengths in pyridine at room temperature. The products display strong surface activity and produce a remarkable synergistic stabilization of a fluorocarbon/Pluronic F-68 type emulsion. Biocompatibility data are reported, which include in vitro toxicity tests on Namalva cell cultures and hemolysis tests on human blood cells; the latter was found to decrease as the length of the F-alkyl chain increased. IV injection in mice (n = 10) showed that these products were innocuous at 400-1000 mg/kg of body weight. Preliminary exchange-perfusion experiments on rats with an emulsion containing the F-octyl xylitol ether were encouraging.

  DOI：

  10.1021/jm00166a028

文献信息

• New polyhydroxylated and highly fluorinated compounds, their preparation and their use as surfactants
  申请人：ATTA

  公开号：EP0255443A1

  公开（公告）日：1988-02-03

  Compounds having a polyhydroxylated hydrophilic moiety, a highly fluorinated moiety and a functional junction group linking said moieties together, wherein said hydrophilic moiety is derived from a polyol or an aminopolyol, and wherein said highly fluorinated moiety consists of a fluorocarbon group wherein at least 50 % of the atoms bonded to the carbon skeleton are fluorine atoms, the other atoms bonded to the carbon skeleton being hydrogen, chlorine or bromine atoms, said highly fluorinated moiety containing at least 4 fluorine atoms ; as well as the internal ethers and ketals thereof ; process for their preparation ; and compositions containing said compounds as surfactants together with non polar compounds, for use as gas carriers.

  具有一个多羟基亲水基团、一个高氟化基团和一个将上述基团连接在一起的功能连接基团的化合物，其中所述亲水基团来自多元醇或氨基多元醇，所述高氟化基团由碳氟化合物基团组成，其中与碳骨架结合的原子中至少有 50% 为氟原子，与碳骨架结合的其他原子为氢原子、氯原子或溴原子，所述高氟化基团至少含有 4 个氟原子；及其内醚和酮类；制备方法；以及含有上述化合物作为表面活性剂的组合物和用作气体载体的非极性化合物。
• ZARIF, LEILA;GREINER, JACQUES;PACE, SIMONNE;RIESS, JEAN G., J. MED. CHEM., 33,(1990) N, C. 1262-1269
  作者：ZARIF, LEILA、GREINER, JACQUES、PACE, SIMONNE、RIESS, JEAN G.

  DOI：——

  日期：——
• US4985550A
  申请人：——

  公开号：US4985550A

  公开（公告）日：1991-01-15
• Synthesis of perfluoroalkylated xylitol ethers and esters: new surfactants for biomedical uses
  作者：Leila Zarif、Jacques Greiner、Simonne Pace、Jean G. Riess

  DOI：10.1021/jm00166a028

  日期：1990.4

  New, well-defined surfactants and cosurfactants were synthesized with the objective of enhancing the stability of fluorocarbon emulsions destined to serve as oxygen carriers for biomedical applications. Monoperfluoroalkylated ethers of xylitol were achieved by addition of perfluoroalkyl iodide on the double bond of a protected xylitol allyl ether in a one-step addition-elimination reaction. Monoesters were obtained specifically on position 5 by treating 1,2:3,4-di-O-isopropylidenexylitol with perfluoroalkylated acid chlorides of various chain lengths in pyridine at room temperature. The products display strong surface activity and produce a remarkable synergistic stabilization of a fluorocarbon/Pluronic F-68 type emulsion. Biocompatibility data are reported, which include in vitro toxicity tests on Namalva cell cultures and hemolysis tests on human blood cells; the latter was found to decrease as the length of the F-alkyl chain increased. IV injection in mice (n = 10) showed that these products were innocuous at 400-1000 mg/kg of body weight. Preliminary exchange-perfusion experiments on rats with an emulsion containing the F-octyl xylitol ether were encouraging.