5-[(R)-16-(tert-Butyl-dimethyl-silanyloxy)-heptadecyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one | 185671-85-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 5-[(R)-16-(tert-Butyl-dimethyl-silanyloxy)-heptadecyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one
• 英文别名: 5-[(16R)-16-[tert-butyl(dimethyl)silyl]oxyheptadecyl]-2,2-dimethyl-1,3-benzodioxin-4-one
• CAS: 185671-85-6
• 化学式: C₃₃H₅₈O₄Si
• 分子量: 546.907
• InChiKey: SATLCAOONSGDQU-HHHXNRCGSA-N

物化性质

• 沸点：
  597.6±50.0 °C(Predicted)
• 密度：
  0.950±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.39
• 重原子数：
  38
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[(R)-16-(tert-Butyl-dimethyl-silanyloxy)-heptadecyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 sodium hydride 、 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.25h， 生成 benzyl 2-[(16R)-16-[(2R,3S,4S,5R)-5-[tert-butyl(dimethyl)silyl]oxy-3,4,6-tris(phenylmethoxy)-2-(trifluoromethylsulfonyloxy)hexanoyl]oxyheptadecyl]-6-phenylmethoxybenzoate
  参考文献：
  名称：

  Total Synthesis of Caloporoside

  摘要：

  The first total synthesis of the fungal metabolite caloporoside 1, a strong and selective inhibitor of phospholipase C, is described. Both sugar units of its complex disaccharidic segment were obtained from 3,4,6-tri-O-benzyl-D-glucopyranose 14 as a common building block, with D-gluco-->D-manno inversions as the key strategic elements. This particular substitution reaction occurred readily on the acyclic segment (27-->28), whereas ultrasonication was required to override adverse stereoelectronic effects upon formation of beta-D-mannopyranoside unit 34. The (16R)-hydroxyheptadecylsalicylic acid part of 1 was efficiently prepared by a palladium-catalyzed Suzuki cross coupling reaction of aryltriflate 7 with the 9-alkyl-9-BBN derivative formed from alkene 6 and 9-H-9-BBN.

  DOI：

  10.1021/jo9800098
• 作为产物：
  描述：

  5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 在 吡啶 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 9-BBN dimer 、 sodium methylate 、 potassium bromide 作用下， 反应 0.17h， 生成 5-[(R)-16-(tert-Butyl-dimethyl-silanyloxy)-heptadecyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one
  参考文献：
  名称：

  具有GABA A离子通道受体抑制特性的真菌代谢产物2-羟基-6-{[（（16 R）-β-δ-甘露吡喃基氧基]十七烷基}苯甲酸）的合成

  摘要：

  描述了生理活性真菌代谢物1的快速全合成。六吡喃-2-溴代糖基溴化物15与糖基受体13反应，然后还原所得的β-δ-甘露糖-2-基糖苷16，可通过两个步骤实现其β-δ-甘露吡喃型硅键的立体选择性形成。通过芳基三氟甲磺酸酯11与9-烷基-9-BBN衍生物10的Suzuki反应有效地制备了醇13。

  DOI：

  10.1016/s0040-4020(96)00950-7

文献信息

• Synthesis of 2-hydroxy-6-{[(16R)-β-δ-mannopyransyloxy]heptadecyl}benzoic acid, a fungal metabolite with GABAA ion channel receptor inhibiting properties
  作者：Alois Fürstner、Ingo Konetzki

  DOI：10.1016/s0040-4020(96)00950-7

  日期：1996.11

  An expeditious total synthesis of the physiologically active fungal metabolite 1 is described. The stereoselective formation of its β-δ-mannopyranosidic linkage is achieved in two steps upon reaction of the hexopyranos-2-ulosyl bromide 15 with the glycosyl acceptor 13, followed by reduction of the resulting β-δ-glycos-2-uloside 16. Alcohol 13 was efficiently prepared via a Suzuki reaction of the aryltriflate

  描述了生理活性真菌代谢物1的快速全合成。六吡喃-2-溴代糖基溴化物15与糖基受体13反应，然后还原所得的β-δ-甘露糖-2-基糖苷16，可通过两个步骤实现其β-δ-甘露吡喃型硅键的立体选择性形成。通过芳基三氟甲磺酸酯11与9-烷基-9-BBN衍生物10的Suzuki反应有效地制备了醇13。
• Total Synthesis of Caloporoside
  作者：Alois Fürstner、Ingo Konetzki

  DOI：10.1021/jo9800098

  日期：1998.5.1

  The first total synthesis of the fungal metabolite caloporoside 1, a strong and selective inhibitor of phospholipase C, is described. Both sugar units of its complex disaccharidic segment were obtained from 3,4,6-tri-O-benzyl-D-glucopyranose 14 as a common building block, with D-gluco-->D-manno inversions as the key strategic elements. This particular substitution reaction occurred readily on the acyclic segment (27-->28), whereas ultrasonication was required to override adverse stereoelectronic effects upon formation of beta-D-mannopyranoside unit 34. The (16R)-hydroxyheptadecylsalicylic acid part of 1 was efficiently prepared by a palladium-catalyzed Suzuki cross coupling reaction of aryltriflate 7 with the 9-alkyl-9-BBN derivative formed from alkene 6 and 9-H-9-BBN.