methyl-O-(3,4-di-O-acetyl-2,6-didesoxy-2-iodo-α-L-manno-hexopyranosyl)-(1->4)-2,3,6-tridesoxy-α-L-threo-hex-2-enopyranoside | 127444-69-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl-O-(3,4-di-O-acetyl-2,6-didesoxy-2-iodo-α-L-manno-hexopyranosyl)-(1->4)-2,3,6-tridesoxy-α-L-threo-hex-2-enopyranoside
• CAS: 127444-69-3；142393-23-5；142393-24-6
• 化学式: C₁₇H₂₅IO₈
• 分子量: 484.285
• InChiKey: RPURWBSQMDPWGQ-LCQAZLFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.73
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl-O-(3,4-di-O-acetyl-2,6-didesoxy-2-iodo-α-L-manno-hexopyranosyl)-(1->4)-2,3,6-tridesoxy-α-L-threo-hex-2-enopyranoside 在 吡啶 、 sodium azide 、 三氟甲磺酸三甲基硅酯 、 水 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 46.0h， 生成 methyl-O-(3,4-di-O-acetyl-2,6-didesoxy-2-iodo-α-L-manno-hexopyranosyl)-(1->4)-2,3,6-tridesoxy-3-trifluoroacetamido-β-L-xylo-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：

  methyl 2,3,6-trideoxy-α-L-threo-hex-2-enopyranoside 、 3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 在 N-碘代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以70%的产率得到methyl-O-(3,4-di-O-acetyl-2,6-didesoxy-2-iodo-α-L-manno-hexopyranosyl)-(1->4)-2,3,6-tridesoxy-α-L-threo-hex-2-enopyranoside
  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