(2S,3S,4R)-2-Azido-1-(tert-butyl-diphenyl-silanyloxy)-hexane-3,4-diol | 522615-46-9

• 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: (2S,3S,4R)-2-Azido-1-(tert-butyl-diphenyl-silanyloxy)-hexane-3,4-diol
• 英文别名: (2S,3S,4R)-2-azido-1-[tert-butyl(diphenyl)silyl]oxyhexane-3,4-diol
• CAS: 522615-46-9
• 化学式: C₂₂H₃₁N₃O₃Si
• 分子量: 413.592
• InChiKey: CWBFQZNHZAXXRT-HBMCJLEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  64
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-2-Azido-1-(tert-butyl-diphenyl-silanyloxy)-hexane-3,4-diol 在 palladium on activated charcoal 吡啶 、 氢气 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 69.0h， 生成 Acetic acid (1S,2R)-2-acetoxy-1-((S)-2-acetoxy-1-acetylamino-ethyl)-butyl ester
  参考文献：
  名称：

  A new diorganozinc-based enantioselective access to truncated d-ribo-phytosphingosine

  摘要：

  The use of a trans alpha,beta-epoxyaldehyde as a precursor Of D-ribo-phytosphingosines was studied. The highly stereoselective alkylation of the aldehyde with a diorganozinc reagent was ensured through double asymmetric induction. The regioselective opening of the epoxide in turn gives access to an azide from which a C-10 phytosphingosine can be easily prepared. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02526-1
• 作为产物：
  描述：

  (E)-4-(tert-butyldiphenylsilyloxy)-2-buten-1-ol 在 titanium(IV) isopropylate 、 sodium azide 、 氯化铵 、 1,2-bis(trifluoromethanesulfonamido)cyclohexane 作用下， 以 乙二醇甲醚 、 水 、 甲苯 为溶剂， 反应 25.0h， 生成 (2S,3S,4R)-2-Azido-1-(tert-butyl-diphenyl-silanyloxy)-hexane-3,4-diol
  参考文献：
  名称：

  A new diorganozinc-based enantioselective access to truncated d-ribo-phytosphingosine

  摘要：

  The use of a trans alpha,beta-epoxyaldehyde as a precursor Of D-ribo-phytosphingosines was studied. The highly stereoselective alkylation of the aldehyde with a diorganozinc reagent was ensured through double asymmetric induction. The regioselective opening of the epoxide in turn gives access to an azide from which a C-10 phytosphingosine can be easily prepared. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02526-1

文献信息

• A new diorganozinc-based enantioselective access to truncated d-ribo-phytosphingosine
  作者：Tahar Ayad、Yves Génisson、Alexandre Verdu、Michel Baltas、Liliane Gorrichon

  DOI：10.1016/s0040-4039(02)02526-1

  日期：2003.1

  The use of a trans alpha,beta-epoxyaldehyde as a precursor Of D-ribo-phytosphingosines was studied. The highly stereoselective alkylation of the aldehyde with a diorganozinc reagent was ensured through double asymmetric induction. The regioselective opening of the epoxide in turn gives access to an azide from which a C-10 phytosphingosine can be easily prepared. (C) 2002 Elsevier Science Ltd. All rights reserved.