(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 | 1170692-97-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (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
• CAS: 1170692-97-3
• 化学式: C₇₆H₈₄O₁₅
• 分子量: 1237.49
• InChiKey: RPOVTIVJVNVPCL-ROVMEEILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  91
• 可旋转键数：
  26
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (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 在 palladium dihydroxide 、 氢气 作用下， 生成
  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：

  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
• 作为试剂：
  描述：

  丙烯酸甲酯（MA） 、 苯乙酸甲酯 在 (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 、 sodium t-butanolate 作用下， 生成 dimethyl (S)-2-phenylglutarate 、 dimethyl (R)-2-phenylglutarate
  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.