{(4S,5S)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-3-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol | 471241-80-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: {(4S,5S)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-3-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol
• CAS: 471241-80-2
• 化学式: C₁₆H₃₂O₄Si
• 分子量: 316.513
• InChiKey: QPLGFGZUJUGRTD-MELADBBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  {(4S,5S)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-3-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 36.0h， 生成 Acetic acid (4S,5R)-5-((S)-1-hydroxy-but-3-enyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
  参考文献：
  名称：

  Sequential alkoxy radical fragmentation–intermolecular allylation in carbohydrate systems

  摘要：

  The C-radical originated by beta-fragmentation of carbohydrate anomeric alkoxy radicals, generated under reductive conditions by treatment of N-phthalimido glycosides with allyltri-n-butyltin/AIBN may subsequently undergo ail intermolecular allylation to give hept-1-enitol derivatives. These compounds can be useful chiral synthons for the synthesis of polyhydroxylated compounds. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00911-5
• 作为产物：
  描述：

  2-O-(tert-butyldimethyl)silyl-3,4-O-isopropylidene-1-O-phthalimido-L-arabinopyranose 在 偶氮二异丁腈 作用下， 以 甲醇 、 苯 为溶剂， 反应 26.5h， 生成 {(4S,5S)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-3-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol
  参考文献：
  名称：

  Sequential alkoxy radical fragmentation–intermolecular allylation in carbohydrate systems

  摘要：

  The C-radical originated by beta-fragmentation of carbohydrate anomeric alkoxy radicals, generated under reductive conditions by treatment of N-phthalimido glycosides with allyltri-n-butyltin/AIBN may subsequently undergo ail intermolecular allylation to give hept-1-enitol derivatives. These compounds can be useful chiral synthons for the synthesis of polyhydroxylated compounds. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00911-5