1-<(benzyloxy)methyl>-3,4-dihydro-4-(<3-<<(benzyloxy)methyl>amino>-3-N,4-O-carbonyl-2-deoxy-α-D-allopyranosyl>-1H-indol-3-yl)-3-(1H-indol-3-yl)-1H-pyrrole-2,5-dione | 174290-96-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-<(benzyloxy)methyl>-3,4-dihydro-4-(<3-<<(benzyloxy)methyl>amino>-3-N,4-O-carbonyl-2-deoxy-α-D-allopyranosyl>-1H-indol-3-yl)-3-(1H-indol-3-yl)-1H-pyrrole-2,5-dione
• CAS: 174290-96-1
• 化学式: C₄₃H₃₈N₄O₈
• 分子量: 738.797
• InChiKey: PPBYOWCURYGHNP-SWWZGNLPSA-N

物化性质

• 密度：
  1.42±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.22
• 重原子数：
  55.0
• 可旋转键数：
  12.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  135.56
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-<(benzyloxy)methyl>-3,4-dihydro-4-(<3-<<(benzyloxy)methyl>amino>-3-N,4-O-carbonyl-2-deoxy-α-D-allopyranosyl>-1H-indol-3-yl)-3-(1H-indol-3-yl)-1H-pyrrole-2,5-dione 在 咪唑 、 air 、 potassium tert-butylate 、 碘 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 17.17h， 生成 3'-O,4'-N-carbonyl-3'-O-desmethyl-4'-N-desmethyl-6-N,4'-N-bis<(benzyloxy)methyl>-ent-1'-iodo-7-oxostaurosporine
  参考文献：
  名称：

  Staurosporine and ent-Staurosporine:  The First Total Syntheses, Prospects for a Regioselective Approach, and Activity Profiles¹

  摘要：

  The total syntheses of staurosporine and ent-staurosporine have been achieved. Both glycosidic bonds were built from glycal precursors. The first was constructed by intermolecular coupling of an indole anion with a 1,2-anhydrosugar derived from an endo-glycal by direct epoxidation. The second bond was assembled from an exo-glycal by intramolecular iodoglycosylation.

  DOI：

  10.1021/ja952907g
• 作为产物：
  描述：

  1-<(benzyloxy)methyl>-3,4-dihydro-4-(<3-<<(benzyloxy)methyl>amino>-3-N,4-O-carbonyl-2-deoxy-α-D-allopyranosyl>-1H-indol-3-yl)-3-(1-<2-(trimethylsilyl)ethoxymethyl>-1H-indol-3-yl)-1H-pyrrole-2,5-dione 在 4 A molecular sieve 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以91%的产率得到1-<(benzyloxy)methyl>-3,4-dihydro-4-(<3-<<(benzyloxy)methyl>amino>-3-N,4-O-carbonyl-2-deoxy-α-D-allopyranosyl>-1H-indol-3-yl)-3-(1H-indol-3-yl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Staurosporine and ent-Staurosporine:  The First Total Syntheses, Prospects for a Regioselective Approach, and Activity Profiles¹

  摘要：

  The total syntheses of staurosporine and ent-staurosporine have been achieved. Both glycosidic bonds were built from glycal precursors. The first was constructed by intermolecular coupling of an indole anion with a 1,2-anhydrosugar derived from an endo-glycal by direct epoxidation. The second bond was assembled from an exo-glycal by intramolecular iodoglycosylation.

  DOI：

  10.1021/ja952907g

文献信息

• First Total Synthesis of Staurosporine and ent-Staurosporine
  作者：J. T. Link、Subharekha Raghavan、Samuel J. Danishefsky

  DOI：10.1021/ja00106a072

  日期：1995.1