Benzoic acid (2S,3R,4R,5R)-4-acetoxy-5-(6-benzoylamino-purin-9-yl)-3-(diisopropoxy-phosphorylmethyl)-tetrahydro-furan-2-ylmethyl ester | 244611-81-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: Benzoic acid (2S,3R,4R,5R)-4-acetoxy-5-(6-benzoylamino-purin-9-yl)-3-(diisopropoxy-phosphorylmethyl)-tetrahydro-furan-2-ylmethyl ester
• 英文别名: [(2S,3R,4R,5R)-4-acetyloxy-5-(6-benzamidopurin-9-yl)-3-[di(propan-2-yloxy)phosphorylmethyl]oxolan-2-yl]methyl benzoate
• CAS: 244611-81-2
• 化学式: C₃₃H₃₈N₅O₉P
• 分子量: 679.667
• InChiKey: DRYZHUZKHSFAQO-VSLBMGRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.42
• 重原子数：
  48.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  170.06
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2S,3R,4R,5R)-4-acetoxy-5-(6-benzoylamino-purin-9-yl)-3-(diisopropoxy-phosphorylmethyl)-tetrahydro-furan-2-ylmethyl ester 在 三甲基溴硅烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 [(2S,3S,5R)-5-(6-Amino-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-ylmethyl]-phosphonic acid
  参考文献：
  名称：

  Studies on the Phosphonate Isostere of Nucleoside 3′- and 2′-Phosphates as Precursors of the Related Oligonucleotides

  摘要：

  Synthesis of 2',3'-dideoxy-3'-C-(dihydroxyphosphinylmethyl)-adenosine and -thymidine 5, as well as of 2' -deoxy-2'-C-(dihydroxyphosphinylmethyl)-adenosine and -thymidine 9 was accomplished with the use of the universal carbohydrate precursor 3-deoxy-1,2;5,6-di-O-isopropylidene-3-C-(mesyloxymethyl)-alpha-D-allofuranose (1).

  DOI：

  10.1080/07328319908044681
• 作为产物：
  描述：

  Benzoic acid (2S,3R,4R,5R)-4-acetoxy-5-(6-benzoylamino-purin-9-yl)-3-methanesulfonyloxymethyl-tetrahydro-furan-2-ylmethyl ester 在 sodium iodide 作用下， 生成 Benzoic acid (2S,3R,4R,5R)-4-acetoxy-5-(6-benzoylamino-purin-9-yl)-3-(diisopropoxy-phosphorylmethyl)-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Studies on the Phosphonate Isostere of Nucleoside 3′- and 2′-Phosphates as Precursors of the Related Oligonucleotides

  摘要：

  Synthesis of 2',3'-dideoxy-3'-C-(dihydroxyphosphinylmethyl)-adenosine and -thymidine 5, as well as of 2' -deoxy-2'-C-(dihydroxyphosphinylmethyl)-adenosine and -thymidine 9 was accomplished with the use of the universal carbohydrate precursor 3-deoxy-1,2;5,6-di-O-isopropylidene-3-C-(mesyloxymethyl)-alpha-D-allofuranose (1).

  DOI：

  10.1080/07328319908044681