(S)-3-((2S,4S,5S,6R)-6,7-Dihydroxy-5-methoxymethoxy-2,4-dimethyl-heptanoyl)-4-isopropyl-oxazolidin-2-one | 198289-48-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (S)-3-((2S,4S,5S,6R)-6,7-Dihydroxy-5-methoxymethoxy-2,4-dimethyl-heptanoyl)-4-isopropyl-oxazolidin-2-one
• CAS: 198289-48-4
• 化学式: C₁₇H₃₁NO₇
• 分子量: 361.436
• InChiKey: NOKXRXMGVZNGQV-AHDPXTMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.99
• 重原子数：
  25.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  105.53
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-3-((2S,4S,5S,6R)-6,7-Dihydroxy-5-methoxymethoxy-2,4-dimethyl-heptanoyl)-4-isopropyl-oxazolidin-2-one 在 potassium metaperiodate 、 二异丁基氢化铝 、 potassium hydrogencarbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 31.17h， 生成 ethyl (2E,4S,6S,7S)-9,9-dibromo-7-(methoxymethoxy)-2,4,6-trimethylnona-2,8-dienoate
  参考文献：
  名称：

  A Formal Total Synthesis of (+)-Tetronolide, the Aglycon of the Tetrocarcins:  Enantio- and Diastereoselective Syntheses of the Octahydronaphthalene (Bottom-Half) and Spirotetronate (Top-Half) Fragments

  摘要：

  A formal total synthesis of (+)-tetronolide, the aglycon of the tetrocarcins, has been achieved by virtue of the development of highly diastereo-and enantioselective syntheses of the bottom- and top-half fragments 4 and 5 reported herein. These fragments previously served as key intermediates in Yoshii's pioneering total synthesis of (+)-tetronolide, The synthesis of the bottom-half octahydronaphthalene unit 4 features the intramolecular Diels-Alder reaction of tetraenal 20 and proceeds in 17 steps and 5-6% yield from D-glyceraldehyde pentylidene acetal 8. The synthesis of the spirotetronate fragment 5 features the highly enantioselective exo selective Diels-Alder reaction of triene 37 and chiral dienophile 25b and proceeds in 14 steps and 10% overall yield from cis-2-butene-1,4-diol (38). An enantioselective synthesis of Boeckman's top-half cyclohexene fragment 6 sia the exo selective Diels-Alder reaction of diene 24 and dienophile 25a was also developed, but this route was deemed too inefficient for use in a projected total synthesis of the natural product. The syntheses of 5 and 6 provide important information on the utility of chiral dienophiles 25a and 25b in organic synthesis.

  DOI：

  10.1021/jo970960c
• 作为产物：
  描述：

  (S)-3-[(2S,4S,5S)-5-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-5-methoxymethoxy-2,4-dimethyl-pentanoyl]-4-isopropyl-oxazolidin-2-one 在 甲酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以77%的产率得到(S)-3-((2S,4S,5S,6R)-6,7-Dihydroxy-5-methoxymethoxy-2,4-dimethyl-heptanoyl)-4-isopropyl-oxazolidin-2-one
  参考文献：
  名称：

  A Formal Total Synthesis of (+)-Tetronolide, the Aglycon of the Tetrocarcins:  Enantio- and Diastereoselective Syntheses of the Octahydronaphthalene (Bottom-Half) and Spirotetronate (Top-Half) Fragments

  摘要：

  A formal total synthesis of (+)-tetronolide, the aglycon of the tetrocarcins, has been achieved by virtue of the development of highly diastereo-and enantioselective syntheses of the bottom- and top-half fragments 4 and 5 reported herein. These fragments previously served as key intermediates in Yoshii's pioneering total synthesis of (+)-tetronolide, The synthesis of the bottom-half octahydronaphthalene unit 4 features the intramolecular Diels-Alder reaction of tetraenal 20 and proceeds in 17 steps and 5-6% yield from D-glyceraldehyde pentylidene acetal 8. The synthesis of the spirotetronate fragment 5 features the highly enantioselective exo selective Diels-Alder reaction of triene 37 and chiral dienophile 25b and proceeds in 14 steps and 10% overall yield from cis-2-butene-1,4-diol (38). An enantioselective synthesis of Boeckman's top-half cyclohexene fragment 6 sia the exo selective Diels-Alder reaction of diene 24 and dienophile 25a was also developed, but this route was deemed too inefficient for use in a projected total synthesis of the natural product. The syntheses of 5 and 6 provide important information on the utility of chiral dienophiles 25a and 25b in organic synthesis.

  DOI：

  10.1021/jo970960c