(3R,4S,5S)-5-azido-5-phenyl-3,4-bis(phenylmethoxy)pentanal | 1462855-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R,4S,5S)-5-azido-5-phenyl-3,4-bis(phenylmethoxy)pentanal
• CAS: 1462855-34-0
• 化学式: C₂₅H₂₅N₃O₃
• 分子量: 415.492
• InChiKey: QUHVIEYBUKSJNG-DSNGMDLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S)-5-azido-5-phenyl-3,4-bis(phenylmethoxy)pentanal 、 [ETPP][Br] 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.58h， 以85.714%的产率得到
  参考文献：
  名称：

  First stereoselective total synthesis of triumfettamide

  摘要：

  The first total synthesis of triumfettamide (1) is described. The asymmetric syntheses of two highly functionalized units-alpha-hydroxylated C17 monounsaturated fatty acid unit (2) and C26 phytosphingosine (3) have been accomplished involving Sharpless asymmetric dihydroxylation, Sharpless kinetic resolution, regioselective epoxide opening, regioselective DIBAL-H reduction of acetal, Wittig olefination as the key steps. Finally N-acylation of phytosphingosine 3 with (2R,6Z)-2-hydroxy-6-heptadecenoic acid 2 followed by DDQ deprotection of PMB, provided target compound 1. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.068

文献信息

• First stereoselective total synthesis of triumfettamide
  作者：Thongam Joymati Devi、Bishwajit Saikia、Nabin C. Barua

  DOI：10.1016/j.tet.2013.08.068

  日期：2013.11

  The first total synthesis of triumfettamide (1) is described. The asymmetric syntheses of two highly functionalized units-alpha-hydroxylated C17 monounsaturated fatty acid unit (2) and C26 phytosphingosine (3) have been accomplished involving Sharpless asymmetric dihydroxylation, Sharpless kinetic resolution, regioselective epoxide opening, regioselective DIBAL-H reduction of acetal, Wittig olefination as the key steps. Finally N-acylation of phytosphingosine 3 with (2R,6Z)-2-hydroxy-6-heptadecenoic acid 2 followed by DDQ deprotection of PMB, provided target compound 1. (C) 2013 Elsevier Ltd. All rights reserved.