(4S)-4-[tert-butyl(dimethyl)silyl]oxy-1-[(2R)-6-oxo-2,3-dihydropyran-2-yl]heptane-2,6-dione | 1431375-87-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (4S)-4-[tert-butyl(dimethyl)silyl]oxy-1-[(2R)-6-oxo-2,3-dihydropyran-2-yl]heptane-2,6-dione
• CAS: 1431375-87-9
• 化学式: C₁₈H₃₀O₅Si
• 分子量: 354.519
• InChiKey: CYMQHLVDQKSYJL-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-4-[tert-butyl(dimethyl)silyl]oxy-1-[(2R)-6-oxo-2,3-dihydropyran-2-yl]heptane-2,6-dione 在 吡啶 、 4-二甲氨基吡啶 、 二乙基甲氧基硼烷 、 水 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 12.5h， 生成 (+)-cryptocarya triacetate
  参考文献：
  名称：

  A Unified Synthetic Strategy to the Cryptocarya Family of Natural Products Exploiting Anion Relay Chemistry (ARC)

  摘要：

  A unified synthetic strategy to the Cryptocarya family of natural products has been achieved employing four-component fragment unions in a "single flask" exploiting Anion Relay Chemistry (ARC). Functionalization of the ARC adducts permits rapid construction of five polyhydroxylated di- and tetrahydropyrone natural products of the Cryptocarya class (1-5), in a total of 7-9 steps from commercially available materials.

  DOI：

  10.1021/ol400857k
• 作为产物：
  描述：

  (2R)-1-[2-[(2S)-2-[tert-butyl(dimethyl)silyl]oxy-3-(2-methyl-1,3-dithian-2-yl)propyl]-1,3-dithian-2-yl]pent-4-en-2-ol 在 Hoveyda-Grubbs catalyst second generation 、 水 、 N,N-二异丙基乙胺 、 calcium carbonate 、 mercury dichloride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.33h， 生成 (4S)-4-[tert-butyl(dimethyl)silyl]oxy-1-[(2R)-6-oxo-2,3-dihydropyran-2-yl]heptane-2,6-dione
  参考文献：
  名称：

  A Unified Synthetic Strategy to the Cryptocarya Family of Natural Products Exploiting Anion Relay Chemistry (ARC)

  摘要：

  A unified synthetic strategy to the Cryptocarya family of natural products has been achieved employing four-component fragment unions in a "single flask" exploiting Anion Relay Chemistry (ARC). Functionalization of the ARC adducts permits rapid construction of five polyhydroxylated di- and tetrahydropyrone natural products of the Cryptocarya class (1-5), in a total of 7-9 steps from commercially available materials.

  DOI：

  10.1021/ol400857k

文献信息

• A Unified Synthetic Strategy to the Cryptocarya Family of Natural Products Exploiting Anion Relay Chemistry (ARC)
  作者：Bruno Melillo、Amos B. Smith

  DOI：10.1021/ol400857k

  日期：2013.5.3

  A unified synthetic strategy to the Cryptocarya family of natural products has been achieved employing four-component fragment unions in a "single flask" exploiting Anion Relay Chemistry (ARC). Functionalization of the ARC adducts permits rapid construction of five polyhydroxylated di- and tetrahydropyrone natural products of the Cryptocarya class (1-5), in a total of 7-9 steps from commercially available materials.