O-(3,4-di-O-acetyl-2,6-didesoxy-2-iodo-α-L-talo-hexopyranosyl)-(1->4)-1-O-acetyl-2,3,6-tridesoxy-3-trifluoroacetamido-α-L-arabino-hexopyranose | 142270-43-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(3,4-di-O-acetyl-2,6-didesoxy-2-iodo-α-L-talo-hexopyranosyl)-(1->4)-1-O-acetyl-2,3,6-tridesoxy-3-trifluoroacetamido-α-L-arabino-hexopyranose
• CAS: 142270-43-7
• 化学式: C₂₀H₂₇F₃INO₁₀
• 分子量: 625.335
• InChiKey: MLIPTUPPJQQIRB-UNAXDRORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  135.69
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 O-(3,4-di-O-acetyl-2,6-didesoxy-2-iodo-α-L-talo-hexopyranosyl)-(1->4)-1-O-acetyl-2,3,6-tridesoxy-3-trifluoroacetamido-α-L-arabino-hexopyranose 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以83%的产率得到methyl-O-(3,4-di-O-acetyl-2,6-didesoxy-2-iodo-α-L-talo-hexopyranosyl)-(1->4)-2,3,6-tridesoxy-3-trifluoroacetamido-α-L-arabino-hexopyranoside
  参考文献：
  名称：

  Synthèse de disaccharides polydésoxygénés et iodés

  摘要：

  3-Amino-polydeoxy disaccharides have been prepared by condensation of a glycal with methyl 2,3,6-trideoxy-alpha-L-erythro- (or threo)-hex-2-enopyranoside in the presence of N-iodosuccinimide. After acid hydrolysis of the glycoside, 1,4-addition of hydrazoic acid to the corresponding hex-2-enopyranose led to 3-azido-disaccharides which were acetylated. Reduction of the azido group gave 2,2'-dideoxy- or 2,2'-dideoxy-2'-iodo compounds. Condensation of O-(3,4-di-O-acetyl-2,6-dideoxy-2-iodo-alpha-L-manno-hexopyranosyl)-(1 --> 4)-1-O-acetyl-2,3,6-trideoxy-3-trifluoroacetamido-alpha-L-arabino-hexopyranose with daunomycinone, followed by 3',4'-O-deacetylation produced the new anthracycline, 7-O-[O-(2,6-dideoxy-2-iodo-alpha-L-manno-hexopyranosyl)-(1 --> 4)-2,3,6-trideoxy-3-trifluoroacetamido-alpha-L-arabino-hexopyranosyl]-daunomycinone.

  DOI：

  10.1016/s0008-6215(00)90558-5
• 作为产物：
  描述：

  O-(3,4-di-O-acetyl-2,6-didesoxy-2-iodo-α-L-talo-hexopyranosyl)-(1->4)-3-azido-2,3,6-tridesoxy-L-arabino-hexose 在 吡啶 、 水 、 三乙胺 、 三苯基膦 作用下， 反应 19.0h， 生成 O-(3,4-di-O-acetyl-2,6-didesoxy-2-iodo-α-L-talo-hexopyranosyl)-(1->4)-1-O-acetyl-2,3,6-tridesoxy-3-trifluoroacetamido-α-L-arabino-hexopyranose
  参考文献：
  名称：

  Synthèse de disaccharides polydésoxygénés et iodés

  摘要：

  3-Amino-polydeoxy disaccharides have been prepared by condensation of a glycal with methyl 2,3,6-trideoxy-alpha-L-erythro- (or threo)-hex-2-enopyranoside in the presence of N-iodosuccinimide. After acid hydrolysis of the glycoside, 1,4-addition of hydrazoic acid to the corresponding hex-2-enopyranose led to 3-azido-disaccharides which were acetylated. Reduction of the azido group gave 2,2'-dideoxy- or 2,2'-dideoxy-2'-iodo compounds. Condensation of O-(3,4-di-O-acetyl-2,6-dideoxy-2-iodo-alpha-L-manno-hexopyranosyl)-(1 --> 4)-1-O-acetyl-2,3,6-trideoxy-3-trifluoroacetamido-alpha-L-arabino-hexopyranose with daunomycinone, followed by 3',4'-O-deacetylation produced the new anthracycline, 7-O-[O-(2,6-dideoxy-2-iodo-alpha-L-manno-hexopyranosyl)-(1 --> 4)-2,3,6-trideoxy-3-trifluoroacetamido-alpha-L-arabino-hexopyranosyl]-daunomycinone.

  DOI：

  10.1016/s0008-6215(00)90558-5