Acetic acid (4S,5R)-5-((S)-1-hydroxy-but-3-enyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester | 471241-82-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (4S,5R)-5-((S)-1-hydroxy-but-3-enyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
• CAS: 471241-82-4
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: YKVBBPNJTLARQF-GARJFASQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.01
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-(-)-α-甲氧基苯乙酸 、 Acetic acid (4S,5R)-5-((S)-1-hydroxy-but-3-enyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 (R)-Methoxy-phenyl-acetic acid (S)-1-((4R,5S)-5-acetoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-3-enyl 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 吡啶 、 偶氮二异丁腈 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 62.5h， 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