3'-O,4'-N-carbonyl-3'-O-desmethyl-4'-N-desmethyl-6-N,4'-N-bis<(benzyloxy)methyl>-ent-7-oxostaurosporine | 174291-02-2

• 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: 3'-O,4'-N-carbonyl-3'-O-desmethyl-4'-N-desmethyl-6-N,4'-N-bis<(benzyloxy)methyl>-ent-7-oxostaurosporine
• 英文别名: 3'-O,4'-N-carbonyl-3'-O-desmethyl-4'-N-desmethyl-6-N,4'-N-bis[(benzyloxy)methyl]-ent-7-oxostaurosporine；(2R,3S,7S,9S)-2-methyl-6,20-bis(phenylmethoxymethyl)-4,32-dioxa-1,6,10,20-tetrazanonacyclo[15.12.2.12,9.03,7.010,31.011,16.018,22.023,30.024,29]dotriaconta-11,13,15,17,22,24,26,28,30-nonaene-5,19,21-trione
• CAS: 174291-02-2
• 化学式: C₄₃H₃₄N₄O₇
• 分子量: 718.766
• InChiKey: QWOYAKJUICTZEN-JDKUUGDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.64
• 重原子数：
  54.0
• 可旋转键数：
  8.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  104.47
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3'-O,4'-N-carbonyl-3'-O-desmethyl-4'-N-desmethyl-6-N,4'-N-bis<(benzyloxy)methyl>-ent-7-oxostaurosporine 在 4-二甲氨基吡啶 、 palladium dihydroxide 、 氢气 、 sodium methylate 、 sodium hydride 、 caesium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.75h， 生成 ent-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：

  3'-O,4'-N-carbonyl-3'-O-desmethyl-4'-N-desmethyl-6-N,4'-N-bis<(benzyloxy)methyl>-ent-1'-iodo-7-oxostaurosporine 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 0.5h， 以99%的产率得到3'-O,4'-N-carbonyl-3'-O-desmethyl-4'-N-desmethyl-6-N,4'-N-bis<(benzyloxy)methyl>-ent-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

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