methyl 4-[[(4aR,6S,7R,8S,8aR)-7,8-bis(phenylmethoxy)-2-[4-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononyl)phenyl]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-3,5-dimethoxybenzoate | 1193068-91-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: methyl 4-[[(4aR,6S,7R,8S,8aR)-7,8-bis(phenylmethoxy)-2-[4-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononyl)phenyl]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-3,5-dimethoxybenzoate
• CAS: 1193068-91-5
• 化学式: C₄₆H₄₃F₁₃O₁₀
• 分子量: 1002.82
• InChiKey: OKZDCQCZMPPAAA-OLRUXCLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  69
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  methyl 4-[[(4aR,6S,7R,8S,8aR)-7,8-bis(phenylmethoxy)-2-[4-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononyl)phenyl]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-3,5-dimethoxybenzoate 在 三乙基硅烷 、 二氯苯酚溴酯 作用下， 以 二氯甲烷 为溶剂， 以69%的产率得到
  参考文献：
  名称：

  Total synthesis of macrocyclic glycosides, clemochinenosides A and B, and berchemolide, by fluorous mixture synthesis

  摘要：

  The total synthesis of clemochinenoside A and the first total syntheses of clemochinenoside B and berchemolide were achieved simultaneously via macrocyclization of 4-O-(4-O-(F13)benzyl-beta-D-glucopyranosyl)syringic acid with 4-O-(4-O-(F17)-benzyl-beta-D-glucopyranosyl)vanillic acid by a fluorous mixture synthetic method. The spectroscopic data of the synthetic products were identical with those of the natural products, although the optical rotation of clemochinenoside A differed from the published values in sign and magnitude. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.068
• 作为产物：
  描述：

  、 溴甲苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到methyl 4-[[(4aR,6S,7R,8S,8aR)-7,8-bis(phenylmethoxy)-2-[4-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononyl)phenyl]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-3,5-dimethoxybenzoate
  参考文献：
  名称：

  Total synthesis of macrocyclic glycosides, clemochinenosides A and B, and berchemolide, by fluorous mixture synthesis

  摘要：

  The total synthesis of clemochinenoside A and the first total syntheses of clemochinenoside B and berchemolide were achieved simultaneously via macrocyclization of 4-O-(4-O-(F13)benzyl-beta-D-glucopyranosyl)syringic acid with 4-O-(4-O-(F17)-benzyl-beta-D-glucopyranosyl)vanillic acid by a fluorous mixture synthetic method. The spectroscopic data of the synthetic products were identical with those of the natural products, although the optical rotation of clemochinenoside A differed from the published values in sign and magnitude. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.068