(R)-2-(Trityl-amino)-pentanedioic acid dimethyl ester | 192803-60-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (R)-2-(Trityl-amino)-pentanedioic acid dimethyl ester
• 英文别名: Dimethyl N-(triphenylmethyl)-D-glutamate；dimethyl (2R)-2-(tritylamino)pentanedioate
• CAS: 192803-60-4
• 化学式: C₂₆H₂₇NO₄
• 分子量: 417.505
• InChiKey: VAFPFMDUFOWFRT-HSZRJFAPSA-N

物化性质

• 沸点：
  529.5±50.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-2-(Trityl-amino)-pentanedioic acid dimethyl ester 在 盐酸 、 potassium fluoride 、 lithium aluminium tetrahydride 、 三甲基氯硅烷 、 四丁基氯化铵 、 sodium hydride 、 二异丁基氢化铝 、 三乙胺 、 三氟乙酸 、 sodium iodide 作用下， 以 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 18.5h， 生成 12-carbaeudistomin
  参考文献：
  名称：

  Antiviral and tumor cell antiproliferative SAR studies on tetracyclic eudistomins—II

  摘要：

  In a search for the minimum pharmacophore of the naturally occurring tetracyclic eudistomins, five structural analogues (4-8) were evaluated for their in vitro antiviral and tumor cell antiproliferative activities. For the synthesis of these derivatives both intra- and intermolecular Pictet-Spengler reactions have been used. Opening of the beta-carboline annulated 7-membered D-ring in 6 and 7 resulted in a complete loss of activity. On the other rand, replacement of either the oxygen atom or the sulfur atom in the 7-membered ring by a methylene group in 5 and 8, respectively, is allowed. These results combined with previous SAR data underline the crucial importance of the D-ring in eudistomins as a scaffold for the correct positioning of both basic nitrogen atoms. Also bioisosteric replacement of the bicyclic indole system with a dimethoxyphenyl group, to give the isoquinoline skeleton, is allowed. The tricyclic isoquinoline derivative 4 is, so far, the most promising antiviral analogue; it combines a high potency (MIG at 100 ng/mL (340 nM)) with high MCC/MIC ratios (ranging from 1000 to 5000 against HSV-1, HSV-2, vaccinia virus, and vesicular stomatitis virus). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00034-5
• 作为产物：
  描述：

  D-谷氨酸 在 氯化亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 (R)-2-(Trityl-amino)-pentanedioic acid dimethyl ester
  参考文献：
  名称：

  一种谷氨酸-1-甲酯-5-叔丁酯的合成方法

  摘要：

  本发明公开了一种谷氨酸‑1‑甲酯‑5‑叔丁酯的合成方法，该方法以谷氨酸为起始原料，在甲醇中与氯化亚砜作用下，生成谷氨酸双甲酯；然后将谷氨酸双甲酯与三苯基氯甲烷反应生成氨基被三苯甲基保护的谷氨酸双甲酯，氨基被三苯甲基保护的谷氨酸双甲酯在氢氧化钠的作用下脱掉5位的甲酯，生成三苯甲基‑谷氨酸‑1‑甲酯；三苯甲基‑谷氨酸‑1‑甲酯与三氯乙酰基亚胺叔丁酯反应生成三苯甲基‑谷氨酸‑1‑甲酯‑5‑叔丁酯，三苯甲基‑谷氨酸‑1‑甲酯‑5‑叔丁酯在低浓度的三氟乙酸二氯甲烷溶液中，并加入少量三异丙基硅烷脱掉三苯甲基生成谷氨酸‑1‑甲酯‑5‑叔丁酯。本发明方法操作简单，副产物很少，极易处理，产物产率很高，解决了现有合成方法操作难度大的问题。

  公开号：

  CN109516925B

文献信息

• Simple syntheses of (S)-2- and 4-amino-5-hydroxypentanoic acids
  作者：Kleomenis Barlos、Petros Mamos、Dionysios Papaioannou、Stella Patrianakou

  DOI：10.1039/c39870001583

  日期：——

  The title compounds were efficiently prepared by selective reductions of α- and γ-methyl (S)-N-tritylglutamates with LiAlH4

  通过用LiAlH 4选择性还原α-和γ-甲基（S）-N-三苯甲基谷氨酸盐可以有效地制备标题化合物
• Antiviral and tumor cell antiproliferative SAR studies on tetracyclic eudistomins—II
  作者：Jan H. van Maarseveen、Hans W. Scheeren、Erik De Clercq、Jan Balzarini、Chris G. Kruse

  DOI：10.1016/s0968-0896(97)00034-5

  日期：1997.5

  In a search for the minimum pharmacophore of the naturally occurring tetracyclic eudistomins, five structural analogues (4-8) were evaluated for their in vitro antiviral and tumor cell antiproliferative activities. For the synthesis of these derivatives both intra- and intermolecular Pictet-Spengler reactions have been used. Opening of the beta-carboline annulated 7-membered D-ring in 6 and 7 resulted in a complete loss of activity. On the other rand, replacement of either the oxygen atom or the sulfur atom in the 7-membered ring by a methylene group in 5 and 8, respectively, is allowed. These results combined with previous SAR data underline the crucial importance of the D-ring in eudistomins as a scaffold for the correct positioning of both basic nitrogen atoms. Also bioisosteric replacement of the bicyclic indole system with a dimethoxyphenyl group, to give the isoquinoline skeleton, is allowed. The tricyclic isoquinoline derivative 4 is, so far, the most promising antiviral analogue; it combines a high potency (MIG at 100 ng/mL (340 nM)) with high MCC/MIC ratios (ranging from 1000 to 5000 against HSV-1, HSV-2, vaccinia virus, and vesicular stomatitis virus). (C) 1997 Elsevier Science Ltd.
• 一种谷氨酸-1-甲酯-5-叔丁酯的合成方法
  申请人：陕西慧康生物科技有限责任公司

  公开号：CN109516925B

  公开（公告）日：2021-07-16

  本发明公开了一种谷氨酸‑1‑甲酯‑5‑叔丁酯的合成方法，该方法以谷氨酸为起始原料，在甲醇中与氯化亚砜作用下，生成谷氨酸双甲酯；然后将谷氨酸双甲酯与三苯基氯甲烷反应生成氨基被三苯甲基保护的谷氨酸双甲酯，氨基被三苯甲基保护的谷氨酸双甲酯在氢氧化钠的作用下脱掉5位的甲酯，生成三苯甲基‑谷氨酸‑1‑甲酯；三苯甲基‑谷氨酸‑1‑甲酯与三氯乙酰基亚胺叔丁酯反应生成三苯甲基‑谷氨酸‑1‑甲酯‑5‑叔丁酯，三苯甲基‑谷氨酸‑1‑甲酯‑5‑叔丁酯在低浓度的三氟乙酸二氯甲烷溶液中，并加入少量三异丙基硅烷脱掉三苯甲基生成谷氨酸‑1‑甲酯‑5‑叔丁酯。本发明方法操作简单，副产物很少，极易处理，产物产率很高，解决了现有合成方法操作难度大的问题。