[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[4-[[(2S,3S,4S,6R)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]-3-hydroxy-2-methyloxan-4-yl]carbamoyloxymethyl]-2-nitrophenoxy]oxan-2-yl]methyl acetate | 290304-25-5

• 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: [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[4-[[(2S,3S,4S,6R)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]-3-hydroxy-2-methyloxan-4-yl]carbamoyloxymethyl]-2-nitrophenoxy]oxan-2-yl]methyl acetate
• CAS: 290304-25-5
• 化学式: C₄₉H₅₂N₂O₂₄
• 分子量: 1052.95
• InChiKey: HCAOARAIHZAUKO-GSHGRRSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  75.0
• 可旋转键数：
  15.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  364.95
• 氢给体数：
  5.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[4-[[(2S,3S,4S,6R)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]-3-hydroxy-2-methyloxan-4-yl]carbamoyloxymethyl]-2-nitrophenoxy]oxan-2-yl]methyl acetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以47%的产率得到(8S,10S)-8-乙酰基-7,8,9,10-四氢-6,8,11-三羟基-1-甲氧基-10-[[2,3,6-三脱氧-3-[[[[4-(beta-D-吡喃半乳糖基氧基)-3-硝基苯基]甲氧基]羰基]氨基]-alpha-L-来苏-己糖吡喃糖苷]氧基]-5,12-并四苯醌
  参考文献：
  名称：

  A daunorubicin β-galactoside prodrug for use in conjunction with gene directed enzyme prodrug therapy

  摘要：

  N-[4-(beta-D-Galactopyranosyl)-3-nitrobenzyloxycarbonyl]daunomycin was synthesized as a neutral prodrug of daunomycin. Although stable in 0.05 M phosphate buffer, pH 7.4 at 37 degrees C, it was rapidly converted to daunomycin and 3-nitro-4-hydroxybenzyl alcohol under the same conditions in the presence of E. coli beta-galactosidase. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00742-5
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 sodium tetrahydroborate 、 三乙胺 、 silver(l) oxide 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 、 异丙醇 、 乙腈 为溶剂， 反应 7.92h， 生成 [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[4-[[(2S,3S,4S,6R)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]-3-hydroxy-2-methyloxan-4-yl]carbamoyloxymethyl]-2-nitrophenoxy]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  A daunorubicin β-galactoside prodrug for use in conjunction with gene directed enzyme prodrug therapy

  摘要：

  N-[4-(beta-D-Galactopyranosyl)-3-nitrobenzyloxycarbonyl]daunomycin was synthesized as a neutral prodrug of daunomycin. Although stable in 0.05 M phosphate buffer, pH 7.4 at 37 degrees C, it was rapidly converted to daunomycin and 3-nitro-4-hydroxybenzyl alcohol under the same conditions in the presence of E. coli beta-galactosidase. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00742-5