[(2S,3S,4E,6R)-2-methoxy-4-(2-methoxy-2-oxoethylidene)-2-(2-methyl-1-oxopropan-2-yl)-6-prop-2-enyloxan-3-yl] 3-nitrobenzoate | 849744-81-6

• 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: [(2S,3S,4E,6R)-2-methoxy-4-(2-methoxy-2-oxoethylidene)-2-(2-methyl-1-oxopropan-2-yl)-6-prop-2-enyloxan-3-yl] 3-nitrobenzoate
• CAS: 849744-81-6
• 化学式: C₂₃H₂₇NO₉
• 分子量: 461.469
• InChiKey: VRPWXZUBEHHATO-YDBKPRJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  134
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2S,3S,4E,6R)-2-methoxy-4-(2-methoxy-2-oxoethylidene)-2-(2-methyl-1-oxopropan-2-yl)-6-prop-2-enyloxan-3-yl] 3-nitrobenzoate 在 potassium dioxotetrahydroxoosmate(VI) 咪唑 、 4-二甲氨基吡啶 、 四氧化锇 、 N-甲基吲哚酮 、 hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether 、 二乙基甲氧基硼烷 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 43.17h， 生成 [(2S,3S,4E,6S)-6-[2,3-bis(triethylsilyloxy)propyl]-2-methoxy-4-(2-methoxy-2-oxoethylidene)-2-[(E)-2-methyl-5-oxopent-3-en-2-yl]oxan-3-yl] 3-nitrobenzoate
  参考文献：
  名称：

  Identification of a Tunable Site in Bryostatin Analogs:  C20 Bryologs through Late Stage Diversification

  摘要：

  [GRAPHICS]The C20 region of our bryostatin analogs was identified as a nonpharmacophoric site that could be varied to tune analogs for function and physical properties without significantly affecting their binding affinity for PKC. The use of this site in a late-stage diversification strategy has enabled the facile synthesis of a variety of new C20 analogs, all of which retain nanomolar affinity for PKC, in agreement with our pharmacophore hypothesis.

  DOI：

  10.1021/ol0501931
• 作为产物：
  描述：

  methyl (2E)-2-[(2S,3S,6R)-2-[1-[tert-butyl(dimethyl)silyl]oxy-2-methylpropan-2-yl]-3-hydroxy-2-methoxy-6-prop-2-enyloxan-4-ylidene]acetate 在 4-二甲氨基吡啶 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 达卡巴嗪 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 75.75h， 生成 [(2S,3S,4E,6R)-2-methoxy-4-(2-methoxy-2-oxoethylidene)-2-(2-methyl-1-oxopropan-2-yl)-6-prop-2-enyloxan-3-yl] 3-nitrobenzoate
  参考文献：
  名称：

  Identification of a Tunable Site in Bryostatin Analogs:  C20 Bryologs through Late Stage Diversification

  摘要：

  [GRAPHICS]The C20 region of our bryostatin analogs was identified as a nonpharmacophoric site that could be varied to tune analogs for function and physical properties without significantly affecting their binding affinity for PKC. The use of this site in a late-stage diversification strategy has enabled the facile synthesis of a variety of new C20 analogs, all of which retain nanomolar affinity for PKC, in agreement with our pharmacophore hypothesis.

  DOI：

  10.1021/ol0501931

文献信息

• Identification of a Tunable Site in Bryostatin Analogs:  C20 Bryologs through Late Stage Diversification
  作者：Paul A. Wender、Jeremy L. Baryza

  DOI：10.1021/ol0501931

  日期：2005.3.1

  [GRAPHICS]The C20 region of our bryostatin analogs was identified as a nonpharmacophoric site that could be varied to tune analogs for function and physical properties without significantly affecting their binding affinity for PKC. The use of this site in a late-stage diversification strategy has enabled the facile synthesis of a variety of new C20 analogs, all of which retain nanomolar affinity for PKC, in agreement with our pharmacophore hypothesis.