(3S)-3-{(4R)-2,2-dimethyl-[1,3]dioxolan-4-yl}-3-hydroxy-2-nitropropionic acid ethyl ester | 654083-10-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S)-3-{(4R)-2,2-dimethyl-[1,3]dioxolan-4-yl}-3-hydroxy-2-nitropropionic acid ethyl ester
• CAS: 654083-10-0
• 化学式: C₁₀H₁₇NO₇
• 分子量: 263.247
• InChiKey: OQVGXNLPUSDRBV-OECOWPMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.29
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  108.13
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3S)-3-{(4R)-2,2-dimethyl-[1,3]dioxolan-4-yl}-3-hydroxy-2-nitropropionic acid ethyl ester 在 镍 氢气 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (2S,3S)-2-amino-3-{(4R)-2,2-dimethyl-[1,3]dioxolan-4-yl}-3-[(2R)tetrahydropyran-2-yloxy]propionic acid ethyl ester
  参考文献：
  名称：

  Total synthesis of 3,4-dihydroxyprolines, d-threo-l-norvaline and (2S,3R,4R)-2-amino-3,4-dihydroxytetrahydrofuran-2-carboxylic acid methyl ester

  摘要：

  The Henry reaction between D-glyceraldehyde and ethyl nitroacetate allowed the practical development of a diastereoselective synthesis of 3,4,5-trihydroxy-2-nitropentanoic acid esters, which were reduced to polyoxamic acids, which were used in a new diastereoselective synthesis of 3,4-dihydroxyprolines and new enantioselective syntheses Of D-threo-L-norvaline and (2S,3R,4R)-2-amino-3,4-dihydroxytetrahydrofuran-2-carboxylic acid methyl ester. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.005
• 作为产物：
  描述：

  硝基乙酸乙酯 、 (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 potassium fluoride 作用下， 以 异丙醇 为溶剂， 反应 24.0h， 以45%的产率得到(3S)-3-{(4R)-2,2-dimethyl-[1,3]dioxolan-4-yl}-3-hydroxy-2-nitropropionic acid ethyl ester
  参考文献：
  名称：

  Total synthesis of 3,4-dihydroxyprolines, d-threo-l-norvaline and (2S,3R,4R)-2-amino-3,4-dihydroxytetrahydrofuran-2-carboxylic acid methyl ester

  摘要：

  The Henry reaction between D-glyceraldehyde and ethyl nitroacetate allowed the practical development of a diastereoselective synthesis of 3,4,5-trihydroxy-2-nitropentanoic acid esters, which were reduced to polyoxamic acids, which were used in a new diastereoselective synthesis of 3,4-dihydroxyprolines and new enantioselective syntheses Of D-threo-L-norvaline and (2S,3R,4R)-2-amino-3,4-dihydroxytetrahydrofuran-2-carboxylic acid methyl ester. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.005

文献信息

• Crude<i>D</i>‐(+)‐Glyceraldehyde Obtained from<i>D</i>‐Mannitol‐Diacetonide by Oxidative Cleavage with Sodium Periodate: Its Reactions with Nucleophilic Species
  作者：Jorge L. de O. Domingos、Guilherme V. M. de A. Vilela、Paulo R. R. Costa、Ayres G. Dias

  DOI：10.1081/scc-120027706

  日期：2004.12.31

  The oxidative cleavage of D-(+)-mannitol-diacetonide with sodium periodate lead to a mixture of D-(+)-glyceraldehyde, its hydrate and oligomeric derivatives. In spite of the low concentration of free glyceraldehyde (estimated in similar to20%, by NMR), good yields were obtained in nucleophilic additions involving this mixture and a variety of nucleophiles (amines, phosphonates, phosphoranes, nitronates, organometallic compounds).