2'-deoxy-D-erythro-pentopyranosyldaunomycinone | 68323-13-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 蒽环类药物
• 英文名称: 2'-deoxy-D-erythro-pentopyranosyldaunomycinone
• 英文别名: (7S,9S)-9-acetyl-7-[(2S,4S,5R)-4,5-dihydroxyoxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
• CAS: 68323-13-7
• 化学式: C₂₆H₂₆O₁₁
• 分子量: 514.486
• InChiKey: VSKLNBMTCNVBDG-AJHZBIATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  180
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  柔红酮 在 3 A molecular sieve 、 sodium methylate 、 氰化汞 、 mercury dibromide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.83h， 生成 2'-deoxy-D-erythro-pentopyranosyldaunomycinone
  参考文献：
  名称：

  Synthesis of 2'-deoxy-L-fucopyranosylcarminomycinone and -.epsilon.-pyrromycinone as well as 2'-deoxy-D-erythro-pentopyranosyldaunomycinone, -carminomycinone, and -.epsilon.-pyrromycinone

  摘要：

  Treatment of di-O-acetyl-2-deoxy-L-fucopyranosyl bromide with carminomycinone and epsilon-pyrromycinone in the presence of mercuric bromide and mercuric cyanide afforded 3',4'-diO-acetyl-2'-deoxy-L-fucopyranosylcarminomycinone and -epsilon-pyrromycinone. Similarly, when di-O-acetyl-2-deoxy-D-erythrho-pentopyranosyl chloride was treated with daunomycinone, carminomycinone and epsilon-pyrromycinone, the di-O-acetyl derivatives of the anthracyclinone glycosides were obtained. Deacetylation of the previous acetates with sodium methoxide afforded 2'-deoxy-L-fucopyranosylcarminomycinone and -epsilon-pyrromycinone, as well as 2'-deoxy-D-erythro-pentopyranosyldaunomycinone, -carminomycinone, and -epsilon-pyrromycinone. 2'-Deoxy-L-fucopyranosylcarminomycinone was found to be more active than carminomycin at higher dosages on L1210.

  DOI：

  10.1021/jm00133a023

文献信息

• Synthesis of 2'-deoxy-L-fucopyranosylcarminomycinone and -.epsilon.-pyrromycinone as well as 2'-deoxy-D-erythro-pentopyranosyldaunomycinone, -carminomycinone, and -.epsilon.-pyrromycinone
  作者：Hassan S. El Khadem、David L. Swartz

  DOI：10.1021/jm00133a023

  日期：1981.1

  Treatment of di-O-acetyl-2-deoxy-L-fucopyranosyl bromide with carminomycinone and epsilon-pyrromycinone in the presence of mercuric bromide and mercuric cyanide afforded 3',4'-diO-acetyl-2'-deoxy-L-fucopyranosylcarminomycinone and -epsilon-pyrromycinone. Similarly, when di-O-acetyl-2-deoxy-D-erythrho-pentopyranosyl chloride was treated with daunomycinone, carminomycinone and epsilon-pyrromycinone, the di-O-acetyl derivatives of the anthracyclinone glycosides were obtained. Deacetylation of the previous acetates with sodium methoxide afforded 2'-deoxy-L-fucopyranosylcarminomycinone and -epsilon-pyrromycinone, as well as 2'-deoxy-D-erythro-pentopyranosyldaunomycinone, -carminomycinone, and -epsilon-pyrromycinone. 2'-Deoxy-L-fucopyranosylcarminomycinone was found to be more active than carminomycin at higher dosages on L1210.