(3S)-3-{(4R)-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-nitro-3-(tetrahydropyran-2-yloxy)propionic acid ethyl ester | 654083-11-1

• 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}-2-nitro-3-(tetrahydropyran-2-yloxy)propionic acid ethyl ester
• CAS: 654083-11-1
• 化学式: C₁₅H₂₅NO₈
• 分子量: 347.365
• InChiKey: VJMVWWUMFYVLJW-IKWCTNDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.26
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  106.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (3S)-3-{(4R)-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-nitro-3-(tetrahydropyran-2-yloxy)propionic acid ethyl ester 在 镍 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 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 、 (2S,3S)-2-amino-3-{(4R)-2,2-dimethyl-[1,3]dioxolan-4-yl}-3-[(2S)tetrahydropyran-2-yloxy]propionic acid ethyl ester 、 (2R,3S)-2-amino-3-{(4R)-2,2-dimethyl-[1,3]dioxolan-4-yl}-3-[(2R)tetrahydropyran-2-yloxy]propionic acid ethyl ester 、 (2R,3S)-2-amino-3-{(4R)-2,2-dimethyl-[1,3]dioxolan-4-yl}-3-[(2S)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：

  (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 potassium fluoride 、 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 38.0h， 生成 (3S)-3-{(4R)-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-nitro-3-(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