methyl (2S)-3-(1H-indol-3-yl)-2-[(2-sulfanylidene-1,3,2lambda5-oxathiaphospholan-2-yl)amino]propanoate | 320725-60-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S)-3-(1H-indol-3-yl)-2-[(2-sulfanylidene-1,3,2lambda5-oxathiaphospholan-2-yl)amino]propanoate
• 英文别名: methyl (2S)-3-(1H-indol-3-yl)-2-[(2-sulfanylidene-1,3,2λ5-oxathiaphospholan-2-yl)amino]propanoate
• CAS: 320725-60-8
• 化学式: C₁₄H₁₇N₂O₃PS₂
• 分子量: 356.406
• InChiKey: IRYQIGOIRFSVFB-SZQRVLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S)-3-(1H-indol-3-yl)-2-[(2-sulfanylidene-1,3,2lambda5-oxathiaphospholan-2-yl)amino]propanoate 在 Oxone 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 2(S)-(hydroxy(3-deoxy-3-azidothymidyl)phosphorylamino)-3-(3-indolyl)propionic acid methyl ester
  参考文献：
  名称：

  Conjugation of amino acid O-methyl esters with AZT-5′-O-phosphorothioate and phosphorodithioate

  摘要：

  Based upon 1,3,2-oxathia(-dithia)phospholane chemistry, 5'-O-derivatisation of AZT with the O-methyl esters of L-phenylalanine and L-tryptophan was performed and the corresponding 5'-aminoacidophosphoramidothioates or phosphoramidodithioates of AZT were obtained in satisfactory yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01635-x
• 作为产物：
  描述：

  2-氯-1,3,2-氧杂硫杂磷杂环戊烷 、 L-色氨酸甲酯 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 吡啶 为溶剂， 以75%的产率得到methyl (2S)-3-(1H-indol-3-yl)-2-[(2-sulfanylidene-1,3,2lambda5-oxathiaphospholan-2-yl)amino]propanoate
  参考文献：
  名称：

  Conjugation of amino acid O-methyl esters with AZT-5′-O-phosphorothioate and phosphorodithioate

  摘要：

  Based upon 1,3,2-oxathia(-dithia)phospholane chemistry, 5'-O-derivatisation of AZT with the O-methyl esters of L-phenylalanine and L-tryptophan was performed and the corresponding 5'-aminoacidophosphoramidothioates or phosphoramidodithioates of AZT were obtained in satisfactory yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01635-x

文献信息

• Oxathiaphospholane Approach to the Synthesis of Conjugates of Amino Acids Methyl Esters with Nucleosides
  作者：Janina Baraniak、Renata Kaczmarek、Ewa Wasilewska、Wojciech J. Stec

  DOI：10.1080/10426500212234

  日期：2002.6.1

  Based upon 1,3,2-oxathiaphospholane chemistry, 5'-O-derivatization of nucleosides with the O-methyl esters of amino acids was performed and corresponding conjugates were obtained in satisfactory yield.
• Conjugation of amino acid O-methyl esters with AZT-5′-O-phosphorothioate and phosphorodithioate
  作者：Janina Baraniak、Renata Kaczmarek、Wojciech J. Stec

  DOI：10.1016/s0040-4039(00)01635-x

  日期：2000.11

  Based upon 1,3,2-oxathia(-dithia)phospholane chemistry, 5'-O-derivatisation of AZT with the O-methyl esters of L-phenylalanine and L-tryptophan was performed and the corresponding 5'-aminoacidophosphoramidothioates or phosphoramidodithioates of AZT were obtained in satisfactory yield. (C) 2000 Elsevier Science Ltd. All rights reserved.