methyl 2-[(1R,2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-7-oxabicyclo[4.1.0]heptan-2-yl]acetate | 201603-56-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-[(1R,2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-7-oxabicyclo[4.1.0]heptan-2-yl]acetate
• CAS: 201603-56-7
• 化学式: C₃₀H₃₂O₆
• 分子量: 488.58
• InChiKey: IDIRFXPAPPORAU-KQNWHWCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-[(1R,2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-7-oxabicyclo[4.1.0]heptan-2-yl]acetate 在 lithium hydroxide 、 三丁基膦 、 dithiobis(pyridin N-dioxide) 、 氧气 、 antimony triphenylsulphide 作用下， 以 四氢呋喃 为溶剂， 反应 4.25h， 生成 ((1R,2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-7-oxabicyclo-[4.1.0]heptan-2-yl)methanol (+)-2,3,4-tri-O-benzylcyclophellitol
  参考文献：
  名称：

  Free Radical Studies and Solutions to the Synthesis of (+)-Cyclophellitol

  摘要：

  D-Xylose serves as a starting material for approaches to the synthesis of the glucosidase inhibitors, (+)-cyclophellitol (1) and (+)-epi-cyclophellitol (2). An investigation of the cyclization of diastereomeric oxiranyl radicals to achieve this goal was moderately successful with the diastereomer that would have led to epi-cyclophellitol undergoing cyclization. An alternative route to cyclophellitol from D-xylose employed Grubbs' ring closure metathesis and radical transformations to complete the synthesis.

  DOI：

  10.1021/jo981211d
• 作为产物：
  描述：

  tert-butyl-dimethyl-[(2R,3R,4S)-2,3,4-tris(phenylmethoxy)hex-5-enoxy]silane 在 lithium hydroxide 、 copper(l) iodide 、 Grubbs catalyst first generation 、 三甲基氯硅烷 、 草酰氯 、 四丁基氟化铵 、 碘 、 sodium carbonate 、 potassium hydrogencarbonate 、 二甲基亚砜 、 三乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 89.58h， 生成 methyl 2-[(1R,2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-7-oxabicyclo[4.1.0]heptan-2-yl]acetate
  参考文献：
  名称：

  Free Radical Studies and Solutions to the Synthesis of (+)-Cyclophellitol

  摘要：

  D-Xylose serves as a starting material for approaches to the synthesis of the glucosidase inhibitors, (+)-cyclophellitol (1) and (+)-epi-cyclophellitol (2). An investigation of the cyclization of diastereomeric oxiranyl radicals to achieve this goal was moderately successful with the diastereomer that would have led to epi-cyclophellitol undergoing cyclization. An alternative route to cyclophellitol from D-xylose employed Grubbs' ring closure metathesis and radical transformations to complete the synthesis.

  DOI：

  10.1021/jo981211d

文献信息

• A Synthesis of (+)-Cyclophellitol from <scp>d</scp>-Xylose
  作者：Frederick E. Ziegler、Yizhe Wang

  DOI：10.1021/jo971998s

  日期：1998.2.1
• Free Radical Studies and Solutions to the Synthesis of (+)-Cyclophellitol
  作者：Frederick E. Ziegler、Yizhe Wang

  DOI：10.1021/jo981211d

  日期：1998.10.1

  D-Xylose serves as a starting material for approaches to the synthesis of the glucosidase inhibitors, (+)-cyclophellitol (1) and (+)-epi-cyclophellitol (2). An investigation of the cyclization of diastereomeric oxiranyl radicals to achieve this goal was moderately successful with the diastereomer that would have led to epi-cyclophellitol undergoing cyclization. An alternative route to cyclophellitol from D-xylose employed Grubbs' ring closure metathesis and radical transformations to complete the synthesis.