methyl (2S,3S,4S,5S,6R)-7-[tert-butyl(dimethyl)silyl]oxy-2,3-dihydroxy-4,5,6-tris(phenylmethoxy)heptanoate | 215303-21-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2S,3S,4S,5S,6R)-7-[tert-butyl(dimethyl)silyl]oxy-2,3-dihydroxy-4,5,6-tris(phenylmethoxy)heptanoate
• CAS: 215303-21-2
• 化学式: C₃₅H₄₈O₈Si
• 分子量: 624.847
• InChiKey: UBNGOPXMDZYXSD-UZYORVLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.66
• 重原子数：
  44
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S,4S,5S,6R)-7-[tert-butyl(dimethyl)silyl]oxy-2,3-dihydroxy-4,5,6-tris(phenylmethoxy)heptanoate 在 lithium hydroxide 、 copper(l) iodide 、 Grubbs catalyst first generation 、 三甲基氯硅烷 、 草酰氯 、 (μ-chloro)(μ-methylene)dimethylaluminum 、 四丁基氟化铵 、 碘 、 potassium hydrogencarbonate 、 二甲基亚砜 、 三乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 甲苯 为溶剂， 反应 83.58h， 生成 (3aR,4R,5S,6R,7S,7aR)-7-iodo-4,5,6-tris(phenylmethoxy)-3a,4,5,6,7,7a-hexahydro-3H-1-benzofuran-2-one
  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 、 甲基磺酰胺 、 水 、 四丁基碘化铵 、 sodium hydride 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 mercury dichloride 、 mercury(II) oxide 、 potassium hexacyanoferrate(III) 作用下， 以 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 63.5h， 生成 methyl (2S,3S,4S,5S,6R)-7-[tert-butyl(dimethyl)silyl]oxy-2,3-dihydroxy-4,5,6-tris(phenylmethoxy)heptanoate
  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.