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

• 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
• 英文别名: (2R,3R,4R,5R,6R)-2-(7-chloroindol-1-yl)-5-methoxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-ol
• 化学式: C₂₉H₃₀ClNO₅
• 分子量: 508.014
• InChiKey: XRCGBLRHZRSHQL-SRUILXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 7-chloro-1-<4-O-methyl-3,6-bis-O-(phenymethyl)-β-D-glucopyranosyl>-1H-indole 在 sodium hydride 作用下， 生成 7-chloro-1-<4-O-methyl-2,3,6-tris-O-(phenymethyl)-β-D-glucopyranosyl>-1H-indole
  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 、 1,5-anhydro-3,6-di-O-benzyl-4-O-methyl-2-deoxy-D-arabino-hex-1-wnopyranose 在 sodium hydride 作用下， 生成 7-chloro-1-<4-O-methyl-3,6-bis-O-(phenymethyl)-β-D-glucopyranosyl>-1H-indole
  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.