(3S,4S,5R,6R)-6-[(tert-butyldimethylsilyl)oxy]methyl-3,4,5-trisbenzyloxy-tetrahydropyran-2-one | 1058108-61-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4S,5R,6R)-6-[(tert-butyldimethylsilyl)oxy]methyl-3,4,5-trisbenzyloxy-tetrahydropyran-2-one
• 英文别名: (3S,4S,5R,6R)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,4,5-tris(phenylmethoxy)oxan-2-one
• CAS: 1058108-61-4
• 化学式: C₃₃H₄₂O₆Si
• 分子量: 562.778
• InChiKey: QOBGJUJDMVPGLT-VKONIRKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.69
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,4S,5R,6R)-6-[(tert-butyldimethylsilyl)oxy]methyl-3,4,5-trisbenzyloxy-tetrahydropyran-2-one 、 乙烯基氯化镁 在 cerium(III) chloride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 以64%的产率得到(3S,4S,5R,6R)-6-(tert-butyldimethylsilyloxymethyl)-3,4,5-tris(benzyloxy)-2-vinyl-tetrahydro-4H-pyran-2-ol
  参考文献：
  名称：

  Syntheses of a partially benzylated derivative of the anhydro-d-altro-heptulose found in Coriaria japonica A and of its analogs

  摘要：

  A partially benzylated derivative of anhydro-D-altro-heptulose found in Coriaria japonica A, which is a synthetically useful unit, was successfully synthesized from a D-mannose derivative by a novel synthetic approach involving the intramolecular O-ketopyranosylation reaction developed by us. This synthetic approach was also applicable to the preparation of its four analogs. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.068
• 作为产物：
  描述：

  (3S,4S,5R,6R)-6-[(tert-butyldimethylsilyl)oxy]methyl-3,4,5-trisbenzyloxy-tetrahydro-4H-pyran-2-ol 在 乙酸酐 、 二甲基亚砜 作用下， 以93%的产率得到(3S,4S,5R,6R)-6-[(tert-butyldimethylsilyl)oxy]methyl-3,4,5-trisbenzyloxy-tetrahydropyran-2-one
  参考文献：
  名称：

  Syntheses of a partially benzylated derivative of the anhydro-d-altro-heptulose found in Coriaria japonica A and of its analogs

  摘要：

  A partially benzylated derivative of anhydro-D-altro-heptulose found in Coriaria japonica A, which is a synthetically useful unit, was successfully synthesized from a D-mannose derivative by a novel synthetic approach involving the intramolecular O-ketopyranosylation reaction developed by us. This synthetic approach was also applicable to the preparation of its four analogs. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.068