(S)-2-azido-3-O-benzyl-1,3-propanediol | 242812-38-0

• 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: (S)-2-azido-3-O-benzyl-1,3-propanediol
• 英文别名: (2S)-2-Azido-3-(phenylmethoxy)-1-propanol；(2S)-2-azido-3-phenylmethoxypropan-1-ol
• CAS: 242812-38-0
• 化学式: C₁₀H₁₃N₃O₂
• 分子量: 207.232
• InChiKey: NZTJTVIWKSTTSE-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  15-[(1R,5S,7R)-7-ethenyl-6,8-dioxabicyclo[3.2.1]oct-2-en-5-yl]pentadecyl methanesulfonate 、 (S)-2-azido-3-O-benzyl-1,3-propanediol 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.25h， 以89%的产率得到(1R,5S,7R)-5-[15-[(2S)-2-azido-3-phenylmethoxypropoxy]pentadecyl]-7-ethenyl-6,8-dioxabicyclo[3.2.1]oct-2-ene
  参考文献：
  名称：

  （+）-去氨二脂基脂质B的合成：2-烯丙基-4-氟苯基助剂在闭环复分解反应中的应用。

  摘要：

  描述了利用缩酮化/闭环复分解（K / RCM）策略合成双屈乳香脂素B。在这项工作的过程中，开发了一种新型的2-烯丙基-4-氟苯基助剂用于闭环复分解（RRCM），提高了RCM的收率。通过互补的二羟基化和环氧化途径将所得的6,8-二氧杂双环[3.2.1]辛烯核选择性官能化，以安装C10轴向醇。该双环缩酮核心通过醚化和带有不饱和α-苯基硒烯基酯的烯烃交叉复分解而进一步官能化，以完成总合成。

  DOI：

  10.1021/jo801666t
• 作为产物：
  描述：

  (R)-(+)-3-苄氧基-1,2-丙二醇 在 叠氮基三甲基硅烷 、 偶氮二甲酸二异丙酯 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (S)-2-azido-3-O-benzyl-1,3-propanediol
  参考文献：
  名称：

  Regioselective and Stereospecific Azidation of 1,2- and 1,3-Diols by Azidotrimethylsilane via a Mitsunobu Reaction

  摘要：

  A one-pot regio- and stereospecific azidation reaction of 1,2- and 1,3-diols with azidotrimethylsilane (Me3SiN3) via a Mitsunobu reaction has been achieved. With 1,2- and 1,3-diols, the reaction of triphenylphosphine, diisopropyl azodicarboxylate, and Me3SiN3 in dichloromethane gave regioselective azidation at C-2 and C-3, respectively, in good yield (74-90% combined yield of 1a + 1b or of 2a + 2b). However, application of the same reaction conditions to a 1,4-diol led to the exclusive formation of the cyclic ether. The regioselectivity of this one-pot reaction is influenced by the solvent, the degree of steric bulk at C-2 of the 1,2-diol or at C-3 of the 1,3-diol, and the presence of electron-donating and electron-withdrawing groups near the secondary carbinol carbon. This selectivity is discussed in terms of the mechanistic model proposed by Mathieu-Pelta and Evans (Mathieu-Pelta, I.; Evans, S. A., Jr. J. Org. Chem. 1898, 57, 3409-3413), which involves reaction of the dioxaphospholane intermediate with Me3SiN3 to form oxyphosphonium ions 4 and 5.

  DOI：

  10.1021/jo9906375

文献信息

• Regioselective and Stereospecific Azidation of 1,2- and 1,3-Diols by Azidotrimethylsilane via a Mitsunobu Reaction
  作者：Linli He、Meni Wanunu、Hoe-Sup Byun、Robert Bittman

  DOI：10.1021/jo9906375

  日期：1999.8.1

  A one-pot regio- and stereospecific azidation reaction of 1,2- and 1,3-diols with azidotrimethylsilane (Me3SiN3) via a Mitsunobu reaction has been achieved. With 1,2- and 1,3-diols, the reaction of triphenylphosphine, diisopropyl azodicarboxylate, and Me3SiN3 in dichloromethane gave regioselective azidation at C-2 and C-3, respectively, in good yield (74-90% combined yield of 1a + 1b or of 2a + 2b). However, application of the same reaction conditions to a 1,4-diol led to the exclusive formation of the cyclic ether. The regioselectivity of this one-pot reaction is influenced by the solvent, the degree of steric bulk at C-2 of the 1,2-diol or at C-3 of the 1,3-diol, and the presence of electron-donating and electron-withdrawing groups near the secondary carbinol carbon. This selectivity is discussed in terms of the mechanistic model proposed by Mathieu-Pelta and Evans (Mathieu-Pelta, I.; Evans, S. A., Jr. J. Org. Chem. 1898, 57, 3409-3413), which involves reaction of the dioxaphospholane intermediate with Me3SiN3 to form oxyphosphonium ions 4 and 5.
• Synthesis of (+)-Didemniserinolipid B: Application of a 2-Allyl-4-fluorophenyl Auxiliary for Relay Ring-Closing Metathesis
  作者：Christopher C. Marvin、Eric A. Voight、Judy M. Suh、Christopher L. Paradise、Steven D. Burke

  DOI：10.1021/jo801666t

  日期：2008.11.7

  work, a novel 2-allyl-4-fluorophenyl auxiliary for relay ring-closing metathesis (RRCM) was developed, which increased the yield of the RCM. The resulting 6,8-dioxabicyclo[3.2.1]octene core was selectively functionalized by complimentary dihydroxylation and epoxidation routes to install the C10 axial alcohol. This bicyclic ketal core was further functionalized by etherification and an alkene cross metathesis

  描述了利用缩酮化/闭环复分解（K / RCM）策略合成双屈乳香脂素B。在这项工作的过程中，开发了一种新型的2-烯丙基-4-氟苯基助剂用于闭环复分解（RRCM），提高了RCM的收率。通过互补的二羟基化和环氧化途径将所得的6,8-二氧杂双环[3.2.1]辛烯核选择性官能化，以安装C10轴向醇。该双环缩酮核心通过醚化和带有不饱和α-苯基硒烯基酯的烯烃交叉复分解而进一步官能化，以完成总合成。