[(2R,3S,5R)-2-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphonoyloxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] benzoate | 102987-86-0

• 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-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphonoyloxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] benzoate
• CAS: 102987-86-0
• 化学式: C₄₈H₄₉N₄O₁₄P
• 分子量: 936.909
• InChiKey: FNWBUDMLJMEFPI-ZVGMXEIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  67
• 可旋转键数：
  18
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  207
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-2-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphonoyloxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] benzoate 生成 胸苷酰(3'->5')胸苷铵盐
  参考文献：
  名称：

  A new and versatile approach to the preparation of valuable deoxynucleoside 3′-phosphite intermediates

  摘要：

  DOI：

  10.1016/s0040-4039(00)84506-2
• 作为产物：
  描述：

  保护胸苷 在 吡啶 、 N-甲基咪唑 、 水 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.42h， 生成 [(2R,3S,5R)-2-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphonoyloxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] benzoate
  参考文献：
  名称：

  New phosphite method: the synthesis of oligodeoxyribonucleotides by use of deoxyribonucleoside 3'-[bis(1,1,1,3,3,3-hexafluoro-2-propyl) phosphites] as new key intermediates

  摘要：

  DOI：

  10.1021/ja00191a056

文献信息

• Use of new phosphonylating and coupling agents in the synthesis of oligodeoxyribonucleotides via the H-phosphonate approach
  作者：Osamu Sakatsume、Hiroshi Yamane、Hiroshi Takaku、Naoki Yamamoto

  DOI：10.1016/s0040-4039(01)93898-5

  日期：1989.1

  Tris(1,1,1,3,3,3-hexafluoro-2-propyl) phosphite was used as a phosphonylating reagent for the preparation of nucleoside 3′-H-phosphonate units. The use of a new coupling reagent, 1,3-dimethyl-2-chloro-imidazolinium chloride (DMCI) for the internucleotidic H-phosphonate bond formation via the H-phosphonate approach is also discussed in detail.

  使用三（1,1,1,3,3,3-六氟-2-丙基）亚磷酸酯作为膦酰化试剂来制备核苷3'-H-膦酸酯单元。还详细讨论了使用新型偶联剂1,3-二甲基-2-氯-咪唑啉鎓氯化物（DMCI）通过H-膦酸酯方法形成核苷酸间H-膦酸酯键的方法。
• Nucleoside H-phosphonates. 13. Studies on 3H-1,2-benzodithiol-3-one derivatives as sulfurizing reagents for H-phosphonate and H-phosphonothioate diesters
  作者：Jacek Stawinski、Mats Thelin

  DOI：10.1021/jo00017a033

  日期：1991.8

  Formation of O-oxidized products during sulfurization of H-phosphonothioate and H-phosphonate diesters with 3H-1,2-benzodithiol-3-one 1,1-dioxide (1) was found to be due to generation of the O-oxidizing agents, most likely 3H-2,1-benzoxathiol-3-one 1-oxide (4) and 3H-2,1-benzoxathiol-3-one (5), during the course of the reactions. Another source of the side products formation may be the disproportionation of 1 that occurs in the presence of triethylamine. To overcome these problems, a new sulfur-transferring reagent, 3H-1,2-benzodithiol-3-one (3), has been developed. Under aqueous reaction conditions, which are compatible with both solution- and solid-phase synthesis of oligonucleotides, the reagent 3 furnished clean and fast conversion of H-phosphonothioate and H-phosphonate diesters into the corresponding phosphorodi- and phosphoromonothioates.
• Kuyl-Yeheskiely, E.; Spierenburg, M.; Elst, H. van der, Recueil des Travaux Chimiques des Pays-Bas, 1986, vol. 105, p. 505 - 506
  作者：Kuyl-Yeheskiely, E.、Spierenburg, M.、Elst, H. van der、Tromp, M.、Marel, G. A. van der、Boom, J. H. van

  DOI：——

  日期：——
• Efimov, V. A.; Kalinkina, A. L.; Chakhmakhcheva, O. G., Russian Journal of Bioorganic Chemistry, 1994, vol. 20, # 3, p. 178 - 180
  作者：Efimov, V. A.、Kalinkina, A. L.、Chakhmakhcheva, O. G.

  DOI：——

  日期：——
• SAKATSUME, OSAMU;YAMANE, HIROSHI;TAKAKU, HIROSHI;YAMAMOTO, NAOKI, TETRAHEDRON LETT., 30,(1989) N6, C. 6375-6378
  作者：SAKATSUME, OSAMU、YAMANE, HIROSHI、TAKAKU, HIROSHI、YAMAMOTO, NAOKI

  DOI：——

  日期：——