(4R,5S)-5-[(1R)-1-hydroxy-6-phenylmethoxyhexyl]-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide | 1269799-00-9

• 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: (4R,5S)-5-[(1R)-1-hydroxy-6-phenylmethoxyhexyl]-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide
• CAS: 1269799-00-9
• 化学式: C₂₁H₃₃NO₅
• 分子量: 379.497
• InChiKey: GLMBHPADUWXWMV-CEXWTWQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,5S)-5-[(1R)-1-hydroxy-6-phenylmethoxyhexyl]-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide 在 甲醇 、 偶氮二甲酸二异丙酯 、 potassium carbonate 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 1.75h， 生成 methyl (2S)-2-[(4R,5R)-2,2-dimethyl-5-(5-phenylmethoxypentyl)-1,3-dioxolan-4-yl]-2-hydroxyacetate
  参考文献：
  名称：

  Formal total synthesis of (+)-didemniserinolipid B

  摘要：

  The formal total synthesis of (+)-didemniserinolipid B, a marine tunicate possessing a 6,8-dioxabicyclo[3.2.1]octane framework, was accomplished starting from L-(+)-tartaric acid. The key transformations in the synthesis include the elaboration of a gamma-hydroxy-amide readily obtained by desymmetrization of tartaric acid bis-amide via the controlled addition of a Grignard reagent followed by stereoselective reduction of the resulting ketone. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.006
• 作为产物：
  描述：

  5-benzyloxy-pentylmagnesium bromide 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.5h， 生成 (4R,5S)-5-[(1R)-1-hydroxy-6-phenylmethoxyhexyl]-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide
  参考文献：
  名称：

  Formal total synthesis of (+)-didemniserinolipid B

  摘要：

  The formal total synthesis of (+)-didemniserinolipid B, a marine tunicate possessing a 6,8-dioxabicyclo[3.2.1]octane framework, was accomplished starting from L-(+)-tartaric acid. The key transformations in the synthesis include the elaboration of a gamma-hydroxy-amide readily obtained by desymmetrization of tartaric acid bis-amide via the controlled addition of a Grignard reagent followed by stereoselective reduction of the resulting ketone. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.006

文献信息

• Formal total synthesis of (+)-didemniserinolipid B
  作者：Kavirayani R. Prasad、Vasudeva Rao Gandi

  DOI：10.1016/j.tetasy.2010.11.006

  日期：2010.12

  The formal total synthesis of (+)-didemniserinolipid B, a marine tunicate possessing a 6,8-dioxabicyclo[3.2.1]octane framework, was accomplished starting from L-(+)-tartaric acid. The key transformations in the synthesis include the elaboration of a gamma-hydroxy-amide readily obtained by desymmetrization of tartaric acid bis-amide via the controlled addition of a Grignard reagent followed by stereoselective reduction of the resulting ketone. (C) 2010 Elsevier Ltd. All rights reserved.