(E)-(2S,3R)-2-Dibenzylamino-octadec-4-ene-1,3-diol | 213828-57-0

• 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: (E)-(2S,3R)-2-Dibenzylamino-octadec-4-ene-1,3-diol
• 英文别名: (E,2S,3R)-2-(dibenzylamino)octadec-4-ene-1,3-diol
• CAS: 213828-57-0
• 化学式: C₃₂H₄₉NO₂
• 分子量: 479.747
• InChiKey: YIVZNVNXXUONNU-YNPRQOMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  35
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-二甲氧基丙烷 、 (E)-(2S,3R)-2-Dibenzylamino-octadec-4-ene-1,3-diol 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 8.0h， 生成 Dibenzyl-[(4R,5S)-2,2-dimethyl-4-((E)-pentadec-1-enyl)-[1,3]dioxan-5-yl]-amine
  参考文献：
  名称：

  A facile stereodivergent synthesis of threo- and erythro-N,N-dibenzyl sphingosines from (S)-N,N-dibenzyl-O-TBDMS-serinal

  摘要：

  The (L)-threo-N,N-dibenzyl sphingosine was prepared in two steps from the serinal derivative 1 by diastereoselective alkenylation with pentadec-l-enyl(ethyl)zinc and deblocking. (D)-erythro-N,N-Dibenzyl sphingosine was also prepared in two steps from 1 by a highly diastereoselective alkynylation with pentadecynyl magnesium bromide and subsequent stereoselective LAH reduction. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00231-6
• 作为产物：
  描述：

  (S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-dibenzylamino-propionaldehyde 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.75h， 生成 (E)-(2S,3R)-2-Dibenzylamino-octadec-4-ene-1,3-diol
  参考文献：
  名称：

  A facile stereodivergent synthesis of threo- and erythro-N,N-dibenzyl sphingosines from (S)-N,N-dibenzyl-O-TBDMS-serinal

  摘要：

  The (L)-threo-N,N-dibenzyl sphingosine was prepared in two steps from the serinal derivative 1 by diastereoselective alkenylation with pentadec-l-enyl(ethyl)zinc and deblocking. (D)-erythro-N,N-Dibenzyl sphingosine was also prepared in two steps from 1 by a highly diastereoselective alkynylation with pentadecynyl magnesium bromide and subsequent stereoselective LAH reduction. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00231-6

文献信息

• A facile stereodivergent synthesis of threo- and erythro-N,N-dibenzyl sphingosines from (S)-N,N-dibenzyl-O-TBDMS-serinal
  作者：José M Andrés、Rafael Pedrosa

  DOI：10.1016/s0957-4166(98)00231-6

  日期：1998.7

  The (L)-threo-N,N-dibenzyl sphingosine was prepared in two steps from the serinal derivative 1 by diastereoselective alkenylation with pentadec-l-enyl(ethyl)zinc and deblocking. (D)-erythro-N,N-Dibenzyl sphingosine was also prepared in two steps from 1 by a highly diastereoselective alkynylation with pentadecynyl magnesium bromide and subsequent stereoselective LAH reduction. (C) 1998 Elsevier Science Ltd. All rights reserved.