(E)-(2R,3S)-2-(4-Methoxy-benzylamino)-octadec-4-ene-1,3-diol | 231291-95-5

• 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: (E)-(2R,3S)-2-(4-Methoxy-benzylamino)-octadec-4-ene-1,3-diol
• 英文别名: (E,2R,3S)-2-[(4-methoxyphenyl)methylamino]octadec-4-ene-1,3-diol
• CAS: 231291-95-5
• 化学式: C₂₆H₄₅NO₃
• 分子量: 419.648
• InChiKey: UYPXPKPKKFWNCZ-QLRMLEDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  30
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  61.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-(2R,3S)-2-(4-Methoxy-benzylamino)-octadec-4-ene-1,3-diol 在 ammonium cerium(IV) nitrate 作用下， 生成 dl-erythro-triacetylsphingosine
  参考文献：
  名称：

  Stereoselective synthesis of β-amino alcohols: practical preparation of all four stereomers of N-PMB-protected sphingosine from l- and d-serine

  摘要：

  Serine was efficiently converted to the N-p-methoxybenzyl (PMB) protected alpha'-amino enone derivative 6, which was reduced with Zn(BH4)(2) to the corresponding anti-beta-amino alcohol in >96% de. On the other hand, N-PMB-N-Boc-protected alpha'-amino enone derivative 8 was reduced by NaBH4 to syn-product with a diastereoselectivity of ca. 90%. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00147-0
• 作为产物：
  描述：

  {2-[(R)-3-(4-Methoxy-benzyl)-2,2-dimethyl-oxazolidin-4-yl]-2-oxo-ethyl}-phosphonic acid dimethyl ester 在 盐酸 、 zinc(II) tetrahydroborate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-(2R,3S)-2-(4-Methoxy-benzylamino)-octadec-4-ene-1,3-diol
  参考文献：
  名称：

  Stereoselective synthesis of β-amino alcohols: practical preparation of all four stereomers of N-PMB-protected sphingosine from l- and d-serine

  摘要：

  Serine was efficiently converted to the N-p-methoxybenzyl (PMB) protected alpha'-amino enone derivative 6, which was reduced with Zn(BH4)(2) to the corresponding anti-beta-amino alcohol in >96% de. On the other hand, N-PMB-N-Boc-protected alpha'-amino enone derivative 8 was reduced by NaBH4 to syn-product with a diastereoselectivity of ca. 90%. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00147-0