3,4-dihydro-3-<7-chloro-1-<<2-(trimethylsilyl)ethoxy>methyl>-1H-indol-3-yl>-4-(7-chloro-1-(3,6-di-O-benzyl-4-O-methyl-β-D-glucopyranosyl)-1H-indol-3-yl)-1-(benzyloxymethyl)-1H-pyrrole-2,5-dione | 145852-81-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 3,4-dihydro-3-<7-chloro-1-<<2-(trimethylsilyl)ethoxy>methyl>-1H-indol-3-yl>-4-(7-chloro-1-(3,6-di-O-benzyl-4-O-methyl-β-D-glucopyranosyl)-1H-indol-3-yl)-1-(benzyloxymethyl)-1H-pyrrole-2,5-dione
• 英文别名: 3,4-dihydro-3-(7-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indol-3-yl)-4-[7-chloro-1-(3,6-di-O-benzyl-4-O-methyl-β-D-glucopyranosyl)-1H-indol-3-yl]-1-(benzyloxymethyl)-1H-pyrrole-2,5-dione；3-[7-chloro-1-[(2R,3R,4R,5R,6R)-3-hydroxy-5-methoxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]indol-3-yl]-4-[7-chloro-1-(2-trimethylsilylethoxymethyl)indol-3-yl]-1-(phenylmethoxymethyl)pyrrole-2,5-dione
• CAS: 145852-81-9
• 化学式: C₅₅H₅₇Cl₂N₃O₉Si
• 分子量: 1003.06
• InChiKey: SDQUXRIVHKWYLK-NOPBVMOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.74
• 重原子数：
  70
• 可旋转键数：
  20
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-3-<7-chloro-1-<<2-(trimethylsilyl)ethoxy>methyl>-1H-indol-3-yl>-4-(7-chloro-1-(3,6-di-O-benzyl-4-O-methyl-β-D-glucopyranosyl)-1H-indol-3-yl)-1-(benzyloxymethyl)-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， 以63%的产率得到3,4-dihydro-3-<7-chloro-1H-indol-3-yl>-4-(7-chloro-1-(3,6-di-O-benzyl-4-O-methyl-β-D-glucopyranosyl)-1H-indol-3-yl)-1-(benzyloxymethyl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  A stereoselective synthesis of indole-.beta.-N-glycosides: an application to the synthesis of rebeccamycin

  摘要：

  Sodium salts of indoles have been found to open alpha-1,2-anhydrosugars with inversion yielding indole-beta-N-glycosides. This methodology constitutes a concise route from glycals to the biologically active indole-N-glycosides. An application to the total synthesis of rebeccamycin is described.

  DOI：

  10.1021/jo00054a015
• 作为产物：
  描述：

  7-氯吲哚 在 甲基碘化镁 、 sodium hydride 作用下， 反应 22.25h， 生成 3,4-dihydro-3-<7-chloro-1-<<2-(trimethylsilyl)ethoxy>methyl>-1H-indol-3-yl>-4-(7-chloro-1-(3,6-di-O-benzyl-4-O-methyl-β-D-glucopyranosyl)-1H-indol-3-yl)-1-(benzyloxymethyl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  A stereoselective synthesis of indole-.beta.-N-glycosides: an application to the synthesis of rebeccamycin

  摘要：

  Sodium salts of indoles have been found to open alpha-1,2-anhydrosugars with inversion yielding indole-beta-N-glycosides. This methodology constitutes a concise route from glycals to the biologically active indole-N-glycosides. An application to the total synthesis of rebeccamycin is described.

  DOI：

  10.1021/jo00054a015

文献信息

• A stereoselective synthesis of indole-.beta.-N-glycosides: an application to the synthesis of rebeccamycin
  作者：Michel Gallant、James T. Link、Samuel J. Danishefsky

  DOI：10.1021/jo00054a015

  日期：1993.1

  Sodium salts of indoles have been found to open alpha-1,2-anhydrosugars with inversion yielding indole-beta-N-glycosides. This methodology constitutes a concise route from glycals to the biologically active indole-N-glycosides. An application to the total synthesis of rebeccamycin is described.