O-5'-O-(Di-p-methoxytrityl)thymidin-3'-yl, O-3'-O-(acetyl)thymidin-5'-yl-phosphorodithioate | 118149-25-0

• 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: O-5'-O-(Di-p-methoxytrityl)thymidin-3'-yl, O-3'-O-(acetyl)thymidin-5'-yl-phosphorodithioate
• 英文别名: 5'-O-dimethoxytritylthimidine-3'-O(5'-O-thymidylyl-3'-O-acetyl) phosphorodithioate；[(2R,3S,5R)-2-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-sulfanylphosphinothioyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate
• CAS: 118149-25-0
• 化学式: C₄₃H₄₇N₄O₁₃PS₂
• 分子量: 922.971
• InChiKey: NGVARBJIQQPQOI-CXPJILFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 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：
  223
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  O-5'-O-(Di-p-methoxytrityl)thymidin-3'-yl, O-3'-O-(acetyl)thymidin-5'-yl-phosphorodithioate 生成 thymidine 3'-O-(5'-O-thymidylyl)phosphorodithioate
  参考文献：
  名称：

  NIELSEN, JOHN;BRILL, WOLFGANG K. -D.;CARUTHERS, MARVIN H., TETRAHEDRON LETT., 29,(1988) N 24, 2911-2914

  摘要：

  DOI：
• 作为产物：
  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]oxy-[2-[methyl(diphenyl)silyl]ethylsulfanyl]phosphinothioyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 生成 O-5'-O-(Di-p-methoxytrityl)thymidin-3'-yl, O-3'-O-(acetyl)thymidin-5'-yl-phosphorodithioate
  参考文献：
  名称：

  Synthesis of Deoxyribonucleoside Phosphorodithioate Dimers by a Triester Method

  摘要：

  DOI：

  10.1080/07328319908044666

文献信息

• Synthesis of oligonucleotide phosphorodithioates
  作者：G. Beaton、W.K.-D. Brill、A. Grandas、Y.-X. Ma、J. Nielsen、E. Yau、M.H. Caruthers

  DOI：10.1016/s0040-4020(01)81775-0

  日期：1991.1

  The synthesis of DNA containing sulfur at the two nonbonding internucleotide valencies is reported. Several different routes using either tervalent or pentavalent mononucleotide synthons are described.

  据报道，在两个非键合核苷酸间价态上合成了含硫的DNA。描述了使用三价或五价单核苷酸合成子的几种不同途径。
• Synthesis and characterization of dinucleoside phosphorodithioates
  作者：John Nielsen、Wolfgang K.-D Brill、Marvin H Caruthers

  DOI：10.1016/0040-4039(88)85045-7

  日期：1988.1

  Dinucleoside phosphoramidites, H2S, and tetrazole react to form dinucleoside H-phosphonothioates. Oxidation with sulfur yields phosphorodithioates. Iodine oxidation in the presence of amines, alcohols, or water yields phosphorothioamidates, thiotriesters or thiodiesters.

  二核苷亚磷酰胺，H 2 S和四唑反应形成二核苷H-硫代磷酸酯。用硫氧化产生二硫代磷酸酯。在胺，醇或水的存在下碘氧化可生成硫代磷酸氨基甲酸酯，硫代三酸酯或硫代二酯。
• Synthesis of Oligo(Deoxyribonucleoside Phosphorodithioate)s by the Dithiaphospholane Approach
  作者：Andrzej Okruszek、Agnieszka Sierzcha-la、Karen L. Fearon、Wojciech J. Stec

  DOI：10.1021/jo00126a060

  日期：1995.10

  A novel method of synthesis of oligo(deoxyribonucleoside phosphorodithioate)s (S-2-ODNs), based on the ring-opening condensation of nucleoside 3'-0-(2-thiono-1,3,2-dithiaphospholane)s with 5'-O-deprotected nucleosi(ti)des in the presence of a strong organic base such as DBU, is presented. The process has been adapted to the requirements of automated solid-phase oligonucleotide synthesis with a relatively short condensation step (5 min) and reasonable step-yield(>95%). N-Methylpyrrolidin-2-ylidenyl (Pya) was found to be the group of choice for the protection of reactive aminofunctions of nucleobases in nucleotide substrates. Sarcosine-containing linker (LCA CPG SAR) was employed due to its known resistance to cleavage by DBU. Several medium-size S-2-ODNs were prepared by this approach. Their identity and purity was confirmed by means of P-31 NMR, gel electrophoresis, and mass spectrometry. It has been demonstrated that, contrary to a recent report, S-2-ODNs are not degraded by DNaseI.
• Dahl, Bjarne H.; Bjergarde, Kirsten; Sommer, Vibeke B., Acta Chemica Scandinavica, 1989, vol. 43, # 9, p. 896 - 901
  作者：Dahl, Bjarne H.、Bjergarde, Kirsten、Sommer, Vibeke B.、Dahl, Otto

  DOI：——

  日期：——
• Brill, Wolfgang K.-D.; Nielsen, John; Caruthers, Marvin H., Journal of the American Chemical Society, 1991, vol. 113, # 10, p. 3972 - 3980
  作者：Brill, Wolfgang K.-D.、Nielsen, John、Caruthers, Marvin H.

  DOI：——

  日期：——