methyl (2R,3R)-3-[(E,1R,2S,3R)-6-methoxy-6-oxo-1,2,3-tris(phenylmethoxy)hex-4-enyl]oxirane-2-carboxylate | 215303-26-7

• 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 (2R,3R)-3-[(E,1R,2S,3R)-6-methoxy-6-oxo-1,2,3-tris(phenylmethoxy)hex-4-enyl]oxirane-2-carboxylate
• CAS: 215303-26-7
• 化学式: C₃₂H₃₄O₈
• 分子量: 546.617
• InChiKey: BYCUICYHFVZQRC-DNILJIKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  40
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  92.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (2R,3R)-3-[(E,1R,2S,3R)-6-methoxy-6-oxo-1,2,3-tris(phenylmethoxy)hex-4-enyl]oxirane-2-carboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到(2R,3R)-3-[(E,1R,2S,3R)-6-methoxy-6-oxo-1,2,3-tris(phenylmethoxy)hex-4-enyl]oxirane-2-carboxylic acid
  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：

  D-xylose diethyl dithioacetal 在 咪唑 、 四氧化锇 、 草酰氯 、 甲基磺酰胺 、 p-nitrosulfonyl chloride 、 氢氟酸 、 水 、 sodium hexamethyldisilazane 、 四丁基碘化铵 、 sodium hydride 、 potassium carbonate 、 二甲基亚砜 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 三乙胺 、 mercury dichloride 、 mercury(II) oxide 、 potassium hexacyanoferrate(III) 作用下， 以 二氯甲烷 、 水 、 丙酮 、 乙腈 、 叔丁醇 为溶剂， 反应 75.58h， 生成 methyl (2R,3R)-3-[(E,1R,2S,3R)-6-methoxy-6-oxo-1,2,3-tris(phenylmethoxy)hex-4-enyl]oxirane-2-carboxylate
  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

• 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.