(S)-2-azido-3-O-p-methoxyphenyl-1,3-propanediol | 213531-28-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-2-azido-3-O-p-methoxyphenyl-1,3-propanediol
• 英文别名: (S)-2-azido-3-O-(4'-methoxyphenyl)-1,3-propanediol；(2S)-2-azido-3-(4-methoxyphenoxy)propan-1-ol
• CAS: 213531-28-3
• 化学式: C₁₀H₁₃N₃O₃
• 分子量: 223.232
• InChiKey: QZMMXJLBWUDLJG-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 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：
  53
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  双(二异丙基氨基)(2-氰基乙氧基)膦 、 3-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-1,2-O-isopropylidene-L-glycerol 、 (S)-2-azido-3-O-p-methoxyphenyl-1,3-propanediol 在 四氮唑 作用下， 以 二氯甲烷 为溶剂， 生成 Phosphorous acid (R)-2-azido-3-(4-methoxy-phenoxy)-propyl ester 2-cyano-ethyl ester (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Synthesis and absolute configuration of a novel aminoglycoglycerolipid, species-specific major immunodeterminant of Mycoplasma fermentans

  摘要：

  In order to determine the absolute configuration of a novel aminoglycoglycerolipid isolated from Mycoplasma fermentans, the possible two diastereomers were stereoselectively synthesized by using (S)- and (R)-glycidols as the key building block. Their H-1-H-1-cosy spectra compared with those of the natural product allowed us to determine the absolute configuration of the glycolipid. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00191-4
• 作为产物：
  描述：

  (R)-3-(p-methoxyphenoxy)-1,2-propanediol 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-p-methoxyphenyl-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