(2R,4S,5R)-4-[[(2R,3R)-3-(hydroxymethyl)-3-methyloxiran-2-yl]methyl]-2-phenyl-1,3-dioxan-5-ol | 1053720-31-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (2R,4S,5R)-4-[[(2R,3R)-3-(hydroxymethyl)-3-methyloxiran-2-yl]methyl]-2-phenyl-1,3-dioxan-5-ol
• CAS: 1053720-31-2
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: DWNAAQHOPOGELR-XLWJZTARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  71.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,4S,5R)-4-[[(2R,3R)-3-(hydroxymethyl)-3-methyloxiran-2-yl]methyl]-2-phenyl-1,3-dioxan-5-ol 在 palladium dihydroxide 、 camphor-10-sulfonic acid 2,6-二甲基吡啶 、 Grubbs catalyst first generation 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 MS-4 Angstroem 、 四丁基氟化铵 、 氢气 、 sodium hexamethyldisilazane 、 4-甲基苯磺酸吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 [(2S,3R,4aS,8aR)-3-(tert-Butyl-dimethyl-silanyloxy)-2,8-dimethyl-2,3,4,4a,6,8a-hexahydro-pyrano[3,2-b]pyran-2-yl]-acetonitrile
  参考文献：
  名称：

  brevetoxin-B的合成研究。第1部分：ABC环系统的立体选择性合成

  摘要：

  短裸-B的ABC-环系统基于所述6-被立体选择性地合成的内切羟基methylepoxide，闭环烯烃复分解和SMI的环化2诱导的还原性分子内环化。

  DOI：

  10.1016/s0040-4039(00)01341-1
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 Oxone 、 Shi's ketone 、 D(+)-10-樟脑磺酸 、 二异丁基氢化铝 、 potassium hydroxide 、 原甲酸三甲酯 作用下， 以 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 25.25h， 生成 (2R,4S,5R)-4-[[(2R,3R)-3-(hydroxymethyl)-3-methyloxiran-2-yl]methyl]-2-phenyl-1,3-dioxan-5-ol
  参考文献：
  名称：

  A Facile and Practical Synthesis of Nicolaou's Key Intermediates, 2-Methyl- and 2,6-Dimethyltetrahydropyrans, toward the Total Synthesis of Ladder-Shaped Polyethers

  摘要：

  A facile and robust method to prepare 2-methyl-and 2,6-dimethyltetrahydropyrans, most useful Nicolaou intermediates for the synthesis of ladder-shaped polyethers, is disclosed. The established highly practical recipe, adopting chemo-and stereoselective catalytic oxidations and one-pot reactions with few chromatographic purifications, would significantly facilitate the large-scale supply of pivotal monocyclic building blocks, which is a rate-determining process of gigantic tetrahydropyran-containing natural products synthesis.

  DOI：

  10.1055/s-0033-1338503

文献信息

• Stereoselective Syntheses of the C‘D‘E‘F‘-Ring System of Maitotoxin and the FG-Ring System of Gambierol
  作者：Yasuharu Sakamoto、Goh Matsuo、Hiroko Matsukura、Tadashi Nakata

  DOI：10.1021/ol016355k

  日期：2001.8.1

  [structure: see text]. The stereoselective syntheses of the C'D'E'F'-ring system of maitotoxin and the FG-ring system of gambierol were accomplished. The key steps involve 6-endo-cyclization of methylepoxide, SmI2-induced reductive cyclization, 6-endo-cyclization of vinylepoxide, and formation of the lactone ring.

  [结构：见文字]。麦托毒素的C'D'E'F'环系统和冈比亚醇的FG环系统完成了立体选择性合成。关键步骤包括甲基环氧化物的6-内环化，SmI2诱导的还原环化，乙烯基环氧化合物的6-内环化以及内酯环的形成。
• Synthetic studies on brevetoxin-B. Part 1: Stereoselective synthesis of the ABC-ring system
  作者：Goh Matsuo、Hiroko Matsukura、Nobuyuki Hori、Tadashi Nakata

  DOI：10.1016/s0040-4039(00)01341-1

  日期：2000.9

  The ABC-ring system of brevetoxin-B was stereoselectively synthesized based on the 6-endo-cyclization of a hydroxy methylepoxide, ring-closing olefin metathesis and SmI2-induced reductive intramolecular cyclization.

  短裸-B的ABC-环系统基于所述6-被立体选择性地合成的内切羟基methylepoxide，闭环烯烃复分解和SMI的环化2诱导的还原性分子内环化。
• A Facile and Practical Synthesis of Nicolaou's Key Intermediates, 2-Methyl- and 2,6-Dimethyltetrahydropyrans, toward the Total Synthesis of Ladder-Shaped Polyethers
  作者：Kohei Torikai、Takeharu Nakashima、Tomomi Baba、Hisaaki Onoue、Wataru Yamashita

  DOI：10.1055/s-0033-1338503

  日期：——

  A facile and robust method to prepare 2-methyl-and 2,6-dimethyltetrahydropyrans, most useful Nicolaou intermediates for the synthesis of ladder-shaped polyethers, is disclosed. The established highly practical recipe, adopting chemo-and stereoselective catalytic oxidations and one-pot reactions with few chromatographic purifications, would significantly facilitate the large-scale supply of pivotal monocyclic building blocks, which is a rate-determining process of gigantic tetrahydropyran-containing natural products synthesis.