(2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-octadecanethioic acid S-tert-butyl ester | 452956-82-0

• 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: (2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-octadecanethioic acid S-tert-butyl ester
• 英文别名: S-tert-butyl (2R,3R,4R,5R)-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2,4-dimethyloctadecanethioate
• CAS: 452956-82-0
• 化学式: C₃₀H₆₂O₃SSi
• 分子量: 530.972
• InChiKey: VPHWDAQGSDXDKK-FICKONGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.77
• 重原子数：
  35
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-octadecanethioic acid S-tert-butyl ester 生成 (2S,3S,4S,5R)-2,4-dimethyloctadecane-1,3,5-triol
  参考文献：
  名称：

  A macrolactonization approach to the stevastelins

  摘要：

  A synthesis of the stevastelins. a novel class of immunosuppressant agents, is reported based on a macrolactonization approach. This synthesis commenced with the stereoselective preparation of the stearic acid segment from tetradecanal using Evans asymmetric synthesis methodology and an aldol reaction with a thioester. After a high yielding coupling reaction between the fatty acid residue and the corresponding tripeptide. we proceeded with the macrolactonization key step. Thus, macrolactonizations of hydroxy acid 27 and dihydroxy acid 30, according to Yamaguchi conditions, afforded the corresponding 13-membered ring stevastelin derivatives 28 and 31 in 90 and 82% yields, respectively. In this latter case, the corresponding 15-membered lactone was not formed. Finally. depsipeptide derivative 31 was converted into stevastelin C3 (5). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00416-1
• 作为产物：
  描述：

  肉豆蔻醛 在 吡啶 、 咪唑 、 锂硼氢 、 草酰氯 、 三氟甲磺酸二丁硼 、 氯代二环己基硼烷 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.5h， 生成 (2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-octadecanethioic acid S-tert-butyl ester
  参考文献：
  名称：

  A macrolactonization approach to the stevastelins

  摘要：

  A synthesis of the stevastelins. a novel class of immunosuppressant agents, is reported based on a macrolactonization approach. This synthesis commenced with the stereoselective preparation of the stearic acid segment from tetradecanal using Evans asymmetric synthesis methodology and an aldol reaction with a thioester. After a high yielding coupling reaction between the fatty acid residue and the corresponding tripeptide. we proceeded with the macrolactonization key step. Thus, macrolactonizations of hydroxy acid 27 and dihydroxy acid 30, according to Yamaguchi conditions, afforded the corresponding 13-membered ring stevastelin derivatives 28 and 31 in 90 and 82% yields, respectively. In this latter case, the corresponding 15-membered lactone was not formed. Finally. depsipeptide derivative 31 was converted into stevastelin C3 (5). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00416-1

文献信息

• A macrolactonization approach to the stevastelins
  作者：Francisco Sarabia、Samy Chammaa、F.Jorge López-Herrera

  DOI：10.1016/s0040-4039(02)00416-1

  日期：2002.4

  A synthesis of the stevastelins. a novel class of immunosuppressant agents, is reported based on a macrolactonization approach. This synthesis commenced with the stereoselective preparation of the stearic acid segment from tetradecanal using Evans asymmetric synthesis methodology and an aldol reaction with a thioester. After a high yielding coupling reaction between the fatty acid residue and the corresponding tripeptide. we proceeded with the macrolactonization key step. Thus, macrolactonizations of hydroxy acid 27 and dihydroxy acid 30, according to Yamaguchi conditions, afforded the corresponding 13-membered ring stevastelin derivatives 28 and 31 in 90 and 82% yields, respectively. In this latter case, the corresponding 15-membered lactone was not formed. Finally. depsipeptide derivative 31 was converted into stevastelin C3 (5). (C) 2002 Elsevier Science Ltd. All rights reserved.