(E)-(3R,6S,9R)-9-Hydroxy-3,6-bis-methoxymethoxy-dec-4-enoic acid | 264889-50-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-(3R,6S,9R)-9-Hydroxy-3,6-bis-methoxymethoxy-dec-4-enoic acid
• 英文别名: (E,3R,6S,9R)-9-hydroxy-3,6-bis(methoxymethoxy)dec-4-enoic acid
• CAS: 264889-50-1
• 化学式: C₁₄H₂₆O₇
• 分子量: 306.356
• InChiKey: DBQHQYAOSLDNMY-LQVFNYONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-(3R,6S,9R)-9-Hydroxy-3,6-bis-methoxymethoxy-dec-4-enoic acid 在 4-二甲氨基吡啶 、 2,4,6-三氯苯甲酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以60%的产率得到(E)-(4R,7S,10R)-4,7-Bis-methoxymethoxy-10-methyl-3,4,7,8,9,10-hexahydro-oxecin-2-one
  参考文献：
  名称：

  Total synthesis of (–)-(3R,6S,9R)-decarestrictine C2

  摘要：

  Enantioselective synthesis of the proposed structure of (-)-(3R,6S,9R)-decarestrictine C-2 (4) has been accomplished using (2S,5S)-1,2,5,6-hexanetetrol (9) as a C-2-symmetric chiral synthon, in which the diastereoselective aldol-type reaction of a tin(II) enolate of 3-acetyl-4(S)-isopropyl-1,3-thiazolidine-2-thione with the alpha,beta-unsaturated aldehyde was used as a key step. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02138-3
• 作为产物：
  描述：

  Toluene-4-sulfonic acid (2S,5S)-2,5,6-trihydroxy-hexyl ester 在 N-乙基哌啶 、 吡啶 、 咪唑 、 lithium aluminium tetrahydride 、 tin(II) trifluoromethanesulfonate 、 草酰氯 、 Amberlyst A-26 (F^(1-)) 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 (E)-(3R,6S,9R)-9-Hydroxy-3,6-bis-methoxymethoxy-dec-4-enoic acid
  参考文献：
  名称：

  Total synthesis of (–)-(3R,6S,9R)-decarestrictine C2

  摘要：

  Enantioselective synthesis of the proposed structure of (-)-(3R,6S,9R)-decarestrictine C-2 (4) has been accomplished using (2S,5S)-1,2,5,6-hexanetetrol (9) as a C-2-symmetric chiral synthon, in which the diastereoselective aldol-type reaction of a tin(II) enolate of 3-acetyl-4(S)-isopropyl-1,3-thiazolidine-2-thione with the alpha,beta-unsaturated aldehyde was used as a key step. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02138-3

文献信息

• Total synthesis of (–)-(3R,6S,9R)-decarestrictine C2
  作者：Mayumi Arai、Nobuyasu Morita、Sakae Aoyagi、Chihiro Kibayashi

  DOI：10.1016/s0040-4039(99)02138-3

  日期：2000.2

  Enantioselective synthesis of the proposed structure of (-)-(3R,6S,9R)-decarestrictine C-2 (4) has been accomplished using (2S,5S)-1,2,5,6-hexanetetrol (9) as a C-2-symmetric chiral synthon, in which the diastereoselective aldol-type reaction of a tin(II) enolate of 3-acetyl-4(S)-isopropyl-1,3-thiazolidine-2-thione with the alpha,beta-unsaturated aldehyde was used as a key step. (C) 2000 Elsevier Science Ltd. All rights reserved.