4-demethoxy-7-O-(3,4-di-O-acetyl-2,6-dideoxy-2-fluoro-α-L-talopyranosyl)daunomycinone | 917364-71-7

• 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: 4-demethoxy-7-O-(3,4-di-O-acetyl-2,6-dideoxy-2-fluoro-α-L-talopyranosyl)daunomycinone
• 英文别名: [(2S,3R,4R,5R,6R)-4-acetyloxy-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]-5-fluoro-2-methyloxan-3-yl] acetate
• CAS: 917364-71-7
• 化学式: C₃₀H₂₉FO₁₂
• 分子量: 600.551
• InChiKey: KSPIDFVFEYXKKS-LDEBZEBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  43
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  183
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  4-demethoxy-7-O-(3,4-di-O-acetyl-2,6-dideoxy-2-fluoro-α-L-talopyranosyl)daunomycinone 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 5.0h， 以78%的产率得到4-demethoxy-7-O-(2,6-dideoxy-2-fluoro-α-L-talopyranosyl)daunomycinone
  参考文献：
  名称：

  Anthracycline glycosides of 2,6-dideoxy-2-fluoro-α-l-talopyranose

  摘要：

  The methyl beta-glycoside of the title sugar, obtained from 2-deoxy-2-fluoro-beta-D-glucopyranose tetraacetate by a sequence with detailed characterization of all intermediates, was converted by acetolysis-bromination into 3,4-di-O-acetyl-2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl bromide, coupling of which with (7S,9S)-4-demethoxydaunomycinone afforded the 3,4-diacetate of 4-demethoxy-9-O-(2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl) daunomycin one (19). The antitumor-active 19 was converted by way of its 14-bromo derivative into the 14-hydroxy analogue, the antitumor-active 4-d emethoxyadriamycin one glycoside 21. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.08.024
• 作为产物：
  描述：

  methyl 2,6-dideoxy-2-fluoro-β-L-talopyranoside 在 硫酸 3 Angstroem MS 、 溴化钛(IV) 、 mercury dibromide 、 mercury(II) oxide 作用下， 以 硝基甲烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 76.0h， 生成 4-demethoxy-7-O-(3,4-di-O-acetyl-2,6-dideoxy-2-fluoro-α-L-talopyranosyl)daunomycinone
  参考文献：
  名称：

  Anthracycline glycosides of 2,6-dideoxy-2-fluoro-α-l-talopyranose

  摘要：

  The methyl beta-glycoside of the title sugar, obtained from 2-deoxy-2-fluoro-beta-D-glucopyranose tetraacetate by a sequence with detailed characterization of all intermediates, was converted by acetolysis-bromination into 3,4-di-O-acetyl-2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl bromide, coupling of which with (7S,9S)-4-demethoxydaunomycinone afforded the 3,4-diacetate of 4-demethoxy-9-O-(2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl) daunomycin one (19). The antitumor-active 19 was converted by way of its 14-bromo derivative into the 14-hydroxy analogue, the antitumor-active 4-d emethoxyadriamycin one glycoside 21. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.08.024

文献信息

• Anthracycline glycosides of 2,6-dideoxy-2-fluoro-α-l-talopyranose
  作者：Derek Horton、Anakshi Khare

  DOI：10.1016/j.carres.2006.08.024

  日期：2006.11

  The methyl beta-glycoside of the title sugar, obtained from 2-deoxy-2-fluoro-beta-D-glucopyranose tetraacetate by a sequence with detailed characterization of all intermediates, was converted by acetolysis-bromination into 3,4-di-O-acetyl-2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl bromide, coupling of which with (7S,9S)-4-demethoxydaunomycinone afforded the 3,4-diacetate of 4-demethoxy-9-O-(2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl) daunomycin one (19). The antitumor-active 19 was converted by way of its 14-bromo derivative into the 14-hydroxy analogue, the antitumor-active 4-d emethoxyadriamycin one glycoside 21. (c) 2006 Elsevier Ltd. All rights reserved.