3',5'-di-O-benzyl-3-N-benzyloxymethyl-3'-C-[2-(phthalimidyloxy)ethyl]-4'-C-(tosyloxymethyl)thymidine | 1161846-15-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3',5'-di-O-benzyl-3-N-benzyloxymethyl-3'-C-[2-(phthalimidyloxy)ethyl]-4'-C-(tosyloxymethyl)thymidine
• 英文别名: [(2S,3S,5R)-3-[2-(1,3-dioxoisoindol-2-yl)oxyethyl]-5-[5-methyl-2,4-dioxo-3-(phenylmethoxymethyl)pyrimidin-1-yl]-3-phenylmethoxy-2-(phenylmethoxymethyl)oxolan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 1161846-15-6
• 化学式: C₅₀H₄₉N₃O₁₂S
• 分子量: 916.018
• InChiKey: RSCFDIIMPKVSFL-IUZSNZOTSA-N

物化性质

• 熔点：
  58-61 °C
• 沸点：
  954.0±75.0 °C(predicted)
• 密度：
  1.41±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  66
• 可旋转键数：
  20
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  176
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3',5'-di-O-benzyl-3-N-benzyloxymethyl-3'-C-[2-(phthalimidyloxy)ethyl]-4'-C-(tosyloxymethyl)thymidine 在 一水合肼 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以93%的产率得到3'-C-[2-(aminoxy)ethyl]-3',5'-di-O-benzyl-3-N-benzyloxymethyl-4'-C-(tosyloxymethyl)thymidine
  参考文献：
  名称：

  Synthesis of a Novel trans-3’,4’-BNA Monomer Bearing a 4,8-Dioxa-5-azabicyclo[5.3.0]decane Skeleton

  摘要：

  A novel trans-3',4'-BNA monomer, in which sugar conformation was restricted to S-type by a trans-fused 3-oxa-4-azapentylene bridge between C3' and C4' position, was designed and synthesized. The trans-fused 7-membered cyclic structure within a 4,8-dioxa-5-azabicyclo[5.3.0]decane skeleton was prepared by means of intramolecular substitution reaction using potassium carbonate as a base. We found that all of protecting groups (benzyl, benzyloxymethyl, and benzyloxycarbonyl group) were able to be removed smoothly by DDQ oxidation followed by boron trichloride treatment without cleavage of N-O linkage to afford the desired trans-3',4'-BNA monomer.

  DOI：

  10.3987/com-08-s(d)58
• 作为产物：
  描述：

  3',5'-di-O-benzyl-3-N-(benzyloxymethyl)-3'-C-(2-hydroxyethyl)-4'-C-(p-toluenesulfonyloxymethyl)thymidine 、 N-羟基邻苯二甲酰亚胺 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.58h， 以90%的产率得到3',5'-di-O-benzyl-3-N-benzyloxymethyl-3'-C-[2-(phthalimidyloxy)ethyl]-4'-C-(tosyloxymethyl)thymidine
  参考文献：
  名称：

  Synthesis of a Novel trans-3’,4’-BNA Monomer Bearing a 4,8-Dioxa-5-azabicyclo[5.3.0]decane Skeleton

  摘要：

  A novel trans-3',4'-BNA monomer, in which sugar conformation was restricted to S-type by a trans-fused 3-oxa-4-azapentylene bridge between C3' and C4' position, was designed and synthesized. The trans-fused 7-membered cyclic structure within a 4,8-dioxa-5-azabicyclo[5.3.0]decane skeleton was prepared by means of intramolecular substitution reaction using potassium carbonate as a base. We found that all of protecting groups (benzyl, benzyloxymethyl, and benzyloxycarbonyl group) were able to be removed smoothly by DDQ oxidation followed by boron trichloride treatment without cleavage of N-O linkage to afford the desired trans-3',4'-BNA monomer.

  DOI：

  10.3987/com-08-s(d)58