[(2R,3S,5R)-2-[[(2S,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]sulfamoyloxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate | 919367-37-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: [(2R,3S,5R)-2-[[(2S,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]sulfamoyloxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate
• CAS: 919367-37-6
• 化学式: C₄₃H₄₇N₅O₁₄S
• 分子量: 889.937
• InChiKey: PGXUUZNBENJAPZ-CXPJILFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  63
• 可旋转键数：
  17
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  235
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-2-[[(2S,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]sulfamoyloxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate 在 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.17h， 生成 [(2R,4S,5R,10S,11S,13R,18R,19S)-18-hydroxy-11-(hydroxymethyl)-18,24-dimethyl-8,8,15,17,22-pentaoxo-7,12,26-trioxa-8lambda6-thia-1,9,14,16,21-pentazapentacyclo[18.2.2.12,5.110,13.014,19]hexacosa-20,23-dien-4-yl] acetate
  参考文献：
  名称：

  Crystal Structure and Photochemical Behavior in Solution of the 3‘-N-Sulfamate Analogue of Thymidylyl(3‘-5‘)thymidine

  摘要：

  [GRAPHICS]The 3'-N-sulfamate analogue of thymidylyl(3'-5')thymidine (TnsoT, 1) exhibits a preference for a C3'-endo conformation in the solution and solid states. Its photochemical behavior in solution is compared to that of its natural counterpart, thymidylyl(3'-5')thymidine (TpT, 2), to get further insight into the significance of the C3'-endo conformation on the photoproduct formation at the single-stranded dinucleotide level. Irradiation at 254 nm of 1 led to the same type of photoproducts as observed with 2. However, 1 was significantly more photoreactive than 2, and accordingly, the initial rate of photoproduct formation was enhanced in accordance with its propensity to base stack compared to 2. The corresponding quantum yields were determined and showed that the enhancement factor (1 compared to 2) is moderate for the cyclobutane pyrimidine dimer (CPD) (1.26) and much higher for the (6-4) photoproduct (1.8). These data strongly suggest that the CPD and (6-4) photoproduct arise from distinct minor stacked conformations.

  DOI：

  10.1021/jo061488a
• 作为产物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-3'-deoxythymidine-3'-sulfamate 、 3'-O-acetylthymidine 在 4 A molecular sieve 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到[(2R,3S,5R)-2-[[(2S,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]sulfamoyloxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate
  参考文献：
  名称：

  Crystal Structure and Photochemical Behavior in Solution of the 3‘-N-Sulfamate Analogue of Thymidylyl(3‘-5‘)thymidine

  摘要：

  [GRAPHICS]The 3'-N-sulfamate analogue of thymidylyl(3'-5')thymidine (TnsoT, 1) exhibits a preference for a C3'-endo conformation in the solution and solid states. Its photochemical behavior in solution is compared to that of its natural counterpart, thymidylyl(3'-5')thymidine (TpT, 2), to get further insight into the significance of the C3'-endo conformation on the photoproduct formation at the single-stranded dinucleotide level. Irradiation at 254 nm of 1 led to the same type of photoproducts as observed with 2. However, 1 was significantly more photoreactive than 2, and accordingly, the initial rate of photoproduct formation was enhanced in accordance with its propensity to base stack compared to 2. The corresponding quantum yields were determined and showed that the enhancement factor (1 compared to 2) is moderate for the cyclobutane pyrimidine dimer (CPD) (1.26) and much higher for the (6-4) photoproduct (1.8). These data strongly suggest that the CPD and (6-4) photoproduct arise from distinct minor stacked conformations.

  DOI：

  10.1021/jo061488a