benzyl 5-deuterio-3-[(1S,2R)-1-hydroxy-3-methoxy-2-(4-nitrophenyl)sulfonyloxy-3-oxopropyl]indole-1-carboxylate | 913967-02-9

• 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: benzyl 5-deuterio-3-[(1S,2R)-1-hydroxy-3-methoxy-2-(4-nitrophenyl)sulfonyloxy-3-oxopropyl]indole-1-carboxylate
• CAS: 913967-02-9
• 化学式: C₂₆H₂₂N₂O₁₀S
• 分子量: 555.526
• InChiKey: JTQMNCUZBDSJED-WJTRKPTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  175
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  benzyl 5-deuterio-3-[(1S,2R)-1-hydroxy-3-methoxy-2-(4-nitrophenyl)sulfonyloxy-3-oxopropyl]indole-1-carboxylate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 以60%的产率得到benzyl 3-[(1S,2S)-2-azido-1-hydroxy-3-methoxy-3-oxopropyl]-5-deuterioindole-1-carboxylate
  参考文献：
  名称：

  Identification and Stereochemical Assignment of the β-Hydroxytryptophan Intermediate in the Echinomycin Biosynthetic Pathway

  摘要：

  Little is known about how quinoxaline-2-carboxylic acid (QC) is synthesized in nature. On the basis of analysis of echinomycin biosynthetic gene clusters as well as feeding experiments with labeled precursors, we have proposed a biosynthetic pathway to QC and identified the (2S,3S)-beta-hydroxytryptophan as a key intermediate.

  DOI：

  10.1021/ol061738+
• 作为产物：
  描述：

  indole-5-d 在 4-二甲氨基吡啶 、 AD-mix-α 、 甲基磺酰胺 、 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 52.5h， 生成 benzyl 5-deuterio-3-[(1S,2R)-1-hydroxy-3-methoxy-2-(4-nitrophenyl)sulfonyloxy-3-oxopropyl]indole-1-carboxylate
  参考文献：
  名称：

  Identification and Stereochemical Assignment of the β-Hydroxytryptophan Intermediate in the Echinomycin Biosynthetic Pathway

  摘要：

  Little is known about how quinoxaline-2-carboxylic acid (QC) is synthesized in nature. On the basis of analysis of echinomycin biosynthetic gene clusters as well as feeding experiments with labeled precursors, we have proposed a biosynthetic pathway to QC and identified the (2S,3S)-beta-hydroxytryptophan as a key intermediate.

  DOI：

  10.1021/ol061738+

文献信息

• Identification and Stereochemical Assignment of the β-Hydroxytryptophan Intermediate in the Echinomycin Biosynthetic Pathway
  作者：Kento Koketsu、Hiroki Oguri、Kenji Watanabe、Hideaki Oikawa

  DOI：10.1021/ol061738+

  日期：2006.10.1

  Little is known about how quinoxaline-2-carboxylic acid (QC) is synthesized in nature. On the basis of analysis of echinomycin biosynthetic gene clusters as well as feeding experiments with labeled precursors, we have proposed a biosynthetic pathway to QC and identified the (2S,3S)-beta-hydroxytryptophan as a key intermediate.