(E)-(3R,6S,9R)-9-(tert-Butyl-diphenyl-silanyloxy)-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-3,6-bis-methoxymethoxy-dec-4-en-1-one | 264889-48-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (E)-(3R,6S,9R)-9-(tert-Butyl-diphenyl-silanyloxy)-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-3,6-bis-methoxymethoxy-dec-4-en-1-one
• 英文别名: (E,3R,6S,9R)-9-[tert-butyl(diphenyl)silyl]oxy-3,6-bis(methoxymethoxy)-1-[(4S)-4-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-3-yl]dec-4-en-1-one
• CAS: 264889-48-7
• 化学式: C₃₆H₅₃NO₆S₂Si
• 分子量: 688.037
• InChiKey: JKDDAJICIQQHHF-SJSSMOEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.54
• 重原子数：
  46
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (E)-(3R,6S,9R)-9-(tert-Butyl-diphenyl-silanyloxy)-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-3,6-bis-methoxymethoxy-dec-4-en-1-one 在 咪唑 、 Amberlyst A-26 (F^(1-)) 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 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
• 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 、 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-(tert-Butyl-diphenyl-silanyloxy)-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-3,6-bis-methoxymethoxy-dec-4-en-1-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

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.