(4S,5S)-5-(2-dimethoxyphosphorylacetyl)-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide | 1315594-73-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (4S,5S)-5-(2-dimethoxyphosphorylacetyl)-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide
• CAS: 1315594-73-0
• 化学式: C₁₂H₂₂NO₈P
• 分子量: 339.282
• InChiKey: BPTJSZNHZNBFCP-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4S,5S)-5-(2-dimethoxyphosphorylacetyl)-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide 在 cerium(III) chloride heptahydrate 、 potassium tri-sec-butyl-borohydride 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 5.66h， 生成 C₂₃H₃₄O₆
  参考文献：
  名称：

  Total Synthesis of (−)-Anamarine

  摘要：

  Total synthesis of polyhydroxy delta-pyranone natural product (-)-anamarine is accomplished from D-(-)-tartaric acid. The main feature of the synthesis is the utility of hitherto unexplored beta-keto phosphonate derived from tartaric acid amide and further elaboration involving stereoselective reduction.

  DOI：

  10.1021/jo2010389
• 作为产物：
  描述：

  甲基膦酸二甲酯 、 (4S,5S)-2,2-Dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid bis-(methoxy-methyl-amide) 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.67h， 以76%的产率得到(4S,5S)-5-(2-dimethoxyphosphorylacetyl)-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide
  参考文献：
  名称：

  Total Synthesis of (−)-Anamarine

  摘要：

  Total synthesis of polyhydroxy delta-pyranone natural product (-)-anamarine is accomplished from D-(-)-tartaric acid. The main feature of the synthesis is the utility of hitherto unexplored beta-keto phosphonate derived from tartaric acid amide and further elaboration involving stereoselective reduction.

  DOI：

  10.1021/jo2010389

文献信息

• Enantiospecific Formal Total Synthesis of Iriomoteolide 3a
  作者：S. Mothish Kumar、Kavirayani R. Prasad

  DOI：10.1002/asia.201402593

  日期：2014.12

  A formal total synthesis of the marine macrolide iriomoteolide 3a is described. Salient features of the synthesis include the elaboration of a β‐keto phosphonate derived from D‐(−)‐tartaric acid and the extension of a chiral butyrolactone derived from L‐glutamic acid. Ring‐closing metathesis is employed to construct the macrolactone core of the natural product.

  描述了海洋大环内酯异烟酰胺3a的正式全合成。合成的显着特征包括衍生自D -（-）-酒石酸的β-酮膦酸酯和衍生自L-谷氨酸的手性丁内酯的延伸。闭环复分解用于构建天然产物的大内酯核。
• Total Synthesis of (−)-Anamarine
  作者：Kavirayani R. Prasad、Kamala Penchalaiah

  DOI：10.1021/jo2010389

  日期：2011.8.19

  Total synthesis of polyhydroxy delta-pyranone natural product (-)-anamarine is accomplished from D-(-)-tartaric acid. The main feature of the synthesis is the utility of hitherto unexplored beta-keto phosphonate derived from tartaric acid amide and further elaboration involving stereoselective reduction.