2-[2-[2-[[(2S,3R,4S,5S,6R)-2-[[(2S,3R,4S,5S,6R)-2-pent-4-enoxy-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methoxy]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methoxy]ethoxy]ethoxy]ethanol | 1170692-93-9

• 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-[2-[2-[[(2S,3R,4S,5S,6R)-2-[[(2S,3R,4S,5S,6R)-2-pent-4-enoxy-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methoxy]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methoxy]ethoxy]ethoxy]ethanol
• CAS: 1170692-93-9
• 化学式: C₈₁H₉₄O₁₆
• 分子量: 1323.63
• InChiKey: ZVUCDGJWXMZLKF-WHBMYGLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  97
• 可旋转键数：
  44
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  159
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  2-[2-[2-[[(2S,3R,4S,5S,6R)-2-[[(2S,3R,4S,5S,6R)-2-pent-4-enoxy-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methoxy]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methoxy]ethoxy]ethoxy]ethanol 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 以48%的产率得到(1R,2S,3S,4R,6S,9S,11R,12S,13S,14R)-1,2,3,12,13,14-hexakis(phenylmethoxy)-4,11-bis(phenylmethoxymethyl)-5,7,10,15,18,21,24-heptaoxadispiro[5.2.59.116]pentacosane
  参考文献：
  名称：

  Transformation of linear oligoketosides into macrocyclic neoglycoconjugates

  摘要：

  The macrocyclization of linear D-galacto-2-heptulopyranose-containing oligoketosides has been carried out by intramolecular glycosidation and ring-closing metathesis. The aglycon fragment of the cyclic neglycoconjugates thus formed was an alkylidene or a polyether chain. One of the oligoketoside-crown ethers showed a moderate asymmetric induction in the Cram model phenyl acetate-acrylate addition. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.056
• 作为产物：
  描述：

  (2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-((2-(2-chloroethoxy)ethoxy)methyl)-2-(((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-(pent-4-en-1-yloxy)tetrahydro-2H-pyran-2-yl)methoxy)tetrahydro-2H-pyran 、 乙二醇 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 14.25h， 生成 2-[2-[2-[[(2S,3R,4S,5S,6R)-2-[[(2S,3R,4S,5S,6R)-2-pent-4-enoxy-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methoxy]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methoxy]ethoxy]ethoxy]ethanol
  参考文献：
  名称：

  Transformation of linear oligoketosides into macrocyclic neoglycoconjugates

  摘要：

  The macrocyclization of linear D-galacto-2-heptulopyranose-containing oligoketosides has been carried out by intramolecular glycosidation and ring-closing metathesis. The aglycon fragment of the cyclic neglycoconjugates thus formed was an alkylidene or a polyether chain. One of the oligoketoside-crown ethers showed a moderate asymmetric induction in the Cram model phenyl acetate-acrylate addition. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.056

文献信息

• Transformation of linear oligoketosides into macrocyclic neoglycoconjugates
  作者：Alessandro Dondoni、Alberto Marra

  DOI：10.1016/j.tetlet.2009.03.056

  日期：2009.7

  The macrocyclization of linear D-galacto-2-heptulopyranose-containing oligoketosides has been carried out by intramolecular glycosidation and ring-closing metathesis. The aglycon fragment of the cyclic neglycoconjugates thus formed was an alkylidene or a polyether chain. One of the oligoketoside-crown ethers showed a moderate asymmetric induction in the Cram model phenyl acetate-acrylate addition. (C) 2009 Elsevier Ltd. All rights reserved.