[(2R,3S,5R)-2-[[[(2R,3S,5R)-5-[4-[[2-(acetyloxymethyl)benzoyl]amino]-2-oxopyrimidin-1-yl]-2-(hydroxymethyl)oxolan-3-yl]oxy-(2-cyanoethoxy)phosphoryl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 4-oxopentanoate | 132164-61-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: [(2R,3S,5R)-2-[[[(2R,3S,5R)-5-[4-[[2-(acetyloxymethyl)benzoyl]amino]-2-oxopyrimidin-1-yl]-2-(hydroxymethyl)oxolan-3-yl]oxy-(2-cyanoethoxy)phosphoryl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 4-oxopentanoate
• CAS: 132164-61-5
• 化学式: C₃₇H₄₃N₆O₁₆P
• 分子量: 858.753
• InChiKey: XEVIHRZCZWXJHG-CXPYHOAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  60.0
• 可旋转键数：
  19.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  295.76
• 氢给体数：
  3.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-2-[[[(2R,3S,5R)-5-[4-[[2-(acetyloxymethyl)benzoyl]amino]-2-oxopyrimidin-1-yl]-2-(hydroxymethyl)oxolan-3-yl]oxy-(2-cyanoethoxy)phosphoryl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 4-oxopentanoate 在 ammonium hydroxide 作用下， 反应 2.0h， 生成 2'-deoxycytosylyl-(3',5')-thymidine ammonium salt
  参考文献：
  名称：

  The 2-(acetoxymethyl)benzoyl (AMB) group as a new base-protecting group, designed for the protection of (phosphate) modified oligonucleotides.

  摘要：

  DOI：

  10.1016/s0040-4039(00)97159-4
• 作为产物：
  描述：

  Acetic acid 2-(1-{(2R,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-2-oxo-1,2-dihydro-pyrimidin-4-ylcarbamoyl)-benzyl ester 生成 [(2R,3S,5R)-2-[[[(2R,3S,5R)-5-[4-[[2-(acetyloxymethyl)benzoyl]amino]-2-oxopyrimidin-1-yl]-2-(hydroxymethyl)oxolan-3-yl]oxy-(2-cyanoethoxy)phosphoryl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 4-oxopentanoate
  参考文献：
  名称：

  The 2-(acetoxymethyl)benzoyl (AMB) group as a new base-protecting group, designed for the protection of (phosphate) modified oligonucleotides.

  摘要：

  DOI：

  10.1016/s0040-4039(00)97159-4

文献信息

• A new strategy for the solid-phase synthesis of 5′-thiolated oligodeoxynucleotides
  作者：Will H.A. Kuijpers、Constant A.A. van Boeckel

  DOI：10.1016/s0040-4020(01)80247-7

  日期：1993.1

  A novel procedure is described for the introduction of a masked thiol function at the 5'-terminus of oligodeoxynucleotides. An acetyl-protected thiol linker phosphoramidite has been prepared which can be coupled efficiently to fully protected oligonucleotides using standard solid-phase techniques. Our strategy is elaborated for oligothymidylates and is further illustrated for oligodeoxynucleotides which are base-protected with the 2-(acetoxymethyl)benzoyl group. Rapid base-deprotection can be accomplished in methanolic potassium carbonate which also effects saponification of the thioacetyl ester. The resultant free thiol is reacted in situ with dithiodipyridine to afford pyridyldisulfide-derivatized oligodeoxynucleotides.
• KUIJPERS, W. H. A.;HUSKENS, J.;BOECKEL, C. A. A. VAN, TETRAHEDRON LETT., 31,(1990) N6, C. 6729-6732
  作者：KUIJPERS, W. H. A.、HUSKENS, J.、BOECKEL, C. A. A. VAN

  DOI：——

  日期：——