[(2S,3S,4R)-5,5-bis(benzylsulfanyl)-1,3,4-tris(phenylmethoxy)pentan-2-yl] methanesulfonate | 144950-27-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2S,3S,4R)-5,5-bis(benzylsulfanyl)-1,3,4-tris(phenylmethoxy)pentan-2-yl] methanesulfonate
• CAS: 144950-27-6
• 化学式: C₄₁H₄₄O₆S₃
• 分子量: 728.995
• InChiKey: UHVHVVGDIJJKLI-KQIHHXPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  50
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(2S,3S,4R)-5,5-bis(benzylsulfanyl)-1,3,4-tris(phenylmethoxy)pentan-2-yl] methanesulfonate 在 四丁基碘化铵 、 barium carbonate 作用下， 反应 1.0h， 生成 benzyl 2,3,5-tri-O-benzyl-1,4-dithio-D-ribofuranoside
  参考文献：
  名称：

  Synthesis and Biological Activity of 4′-Thionucleosides of 2-Chloroadenine¹

  摘要：

  1,2,3,5-Tetra-O-acetyl-4-thio-D-ribofuranose,prepared from 2,3,5-tri-O-benzyl-D-ribofuranose in four steps, was converted to the corresponding 2-chloroadenine nucleoside (8), which was deoxygenated to obtain 2-chloro-2'-deoxy-4'-thioadenosine (12). This is the first report of a 2'-deoxy-4'-thioribonucleoside of a purine rather than a pyrimidine. These novel nucleosides (8 and 12) were cytotoxic to several human tumor cell lines in culture.

  DOI：

  10.1080/15257779408009484
• 作为产物：
  描述：

  2,3,5-三-O-(苯基甲基)-D-呋喃核糖 在 盐酸 、 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 为溶剂， 反应 36.0h， 生成 [(2S,3S,4R)-5,5-bis(benzylsulfanyl)-1,3,4-tris(phenylmethoxy)pentan-2-yl] methanesulfonate
  参考文献：
  名称：

  Synthesis and Biological Activity of 4′-Thionucleosides of 2-Chloroadenine¹

  摘要：

  1,2,3,5-Tetra-O-acetyl-4-thio-D-ribofuranose,prepared from 2,3,5-tri-O-benzyl-D-ribofuranose in four steps, was converted to the corresponding 2-chloroadenine nucleoside (8), which was deoxygenated to obtain 2-chloro-2'-deoxy-4'-thioadenosine (12). This is the first report of a 2'-deoxy-4'-thioribonucleoside of a purine rather than a pyrimidine. These novel nucleosides (8 and 12) were cytotoxic to several human tumor cell lines in culture.

  DOI：

  10.1080/15257779408009484