(2R)-heptadec-16-enol | 185671-83-4

• 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: (2R)-heptadec-16-enol
• 英文别名: (2R)-heptadec-16-en-2-ol
• CAS: 185671-83-4
• 化学式: C₁₇H₃₄O
• 分子量: 254.456
• InChiKey: MMHQTGCODPIGTE-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  18
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2R)-heptadec-16-enol 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 9-borabicyclo[3.3.1]nonane dimer 、 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：

  13-tetradecenyl magnesium bromide 、 (R)-(+)-环氧丙烷 在 CuCl(COD) 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以86%的产率得到(2R)-heptadec-16-enol
  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.