7-chloro-1-<4-O-methyl-3,6-bis-O-(phenymethyl)-β-D-glucopyranosyl>-1H-indole-3-acetamide | 221377-36-2

• 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: 7-chloro-1-<4-O-methyl-3,6-bis-O-(phenymethyl)-β-D-glucopyranosyl>-1H-indole-3-acetamide
• 英文别名: 2-[7-chloro-1-[(2R,3R,4R,5R,6R)-3-hydroxy-5-methoxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]indol-3-yl]acetamide
• CAS: 221377-36-2
• 化学式: C₃₁H₃₃ClN₂O₆
• 分子量: 565.066
• InChiKey: ZDIVIGIYRBCRHH-YKOZYRLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  吲哚-3-乙醛酸甲酯 、 7-chloro-1-<4-O-methyl-3,6-bis-O-(phenymethyl)-β-D-glucopyranosyl>-1H-indole-3-acetamide 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以84%的产率得到3-(1H-indol-3-yl)-4-<7-chloro-1-<4-O-methyl-3,6-bis-O-(phenymethyl)-β-D-glucopyranosyl>-1H-indol-3-yl>-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Synthesis of Rebeccamycin and 11-Dechlororebeccamycin

  摘要：

  Glycosylated 7-chloroindole-3-acetamide 9, prepared in four steps and 26% yield from 7-chloroindole (1), was condensed with methyl 7-chloroindole-3-glyoxylate 11 and methyl indole-3-glyoxylate 12 to provide bisindolylmaleimides 7 and 8 in 86% and 84% yield, respectively. Oxidation of 7 and 8 followed by debenzylation provided a new approach to the synthesis of rebeccamycin and completed for the first time a synthesis of 11-dechlororebeccamycin.

  DOI：

  10.1021/jo982277b
• 作为产物：
  描述：

  7-氯吲哚 在 氢氧化钾 、 sodium hydride 、 乙酸乙酯 作用下， 以 二氯甲烷 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 30.0h， 生成 7-chloro-1-<4-O-methyl-3,6-bis-O-(phenymethyl)-β-D-glucopyranosyl>-1H-indole-3-acetamide
  参考文献：
  名称：

  Synthesis of Rebeccamycin and 11-Dechlororebeccamycin

  摘要：

  Glycosylated 7-chloroindole-3-acetamide 9, prepared in four steps and 26% yield from 7-chloroindole (1), was condensed with methyl 7-chloroindole-3-glyoxylate 11 and methyl indole-3-glyoxylate 12 to provide bisindolylmaleimides 7 and 8 in 86% and 84% yield, respectively. Oxidation of 7 and 8 followed by debenzylation provided a new approach to the synthesis of rebeccamycin and completed for the first time a synthesis of 11-dechlororebeccamycin.

  DOI：

  10.1021/jo982277b

文献信息

• Synthesis of Rebeccamycin and 11-Dechlororebeccamycin
  作者：Margaret M. Faul、Leonard L. Winneroski、Christine A. Krumrich

  DOI：10.1021/jo982277b

  日期：1999.4.1

  Glycosylated 7-chloroindole-3-acetamide 9, prepared in four steps and 26% yield from 7-chloroindole (1), was condensed with methyl 7-chloroindole-3-glyoxylate 11 and methyl indole-3-glyoxylate 12 to provide bisindolylmaleimides 7 and 8 in 86% and 84% yield, respectively. Oxidation of 7 and 8 followed by debenzylation provided a new approach to the synthesis of rebeccamycin and completed for the first time a synthesis of 11-dechlororebeccamycin.