5'-O-(4,4'-dimethoxytrityl)-O6-diphenylcarbamoyl-N2-phenylacetyl-2'-deoxyguanosine | 750629-22-2

• 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: 5'-O-(4,4'-dimethoxytrityl)-O6-diphenylcarbamoyl-N2-phenylacetyl-2'-deoxyguanosine
• 英文别名: 5'-O-(4,4'-dimethoxytrityl)-O⁶-diphenylcarbamoyl-N²-phenylacetyl-2'-deoxyguanosine
• CAS: 750629-22-2
• 化学式: C₅₂H₄₆N₆O₈
• 分子量: 882.973
• InChiKey: ACNPTXKCBQDMTL-UFCNIINJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.02
• 重原子数：
  66.0
• 可旋转键数：
  15.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  159.39
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-O6-diphenylcarbamoyl-N2-phenylacetyl-2'-deoxyguanosine 在 bis(2-oxo-3-oxazolidinyl)phosphoric acid chloride 、 N,N-二异丙基乙胺 、 3-硝基-1,2,4-三氮唑 作用下， 以 四氢呋喃 为溶剂， 生成 tributylammonium 5'-O-dimethoxytrityl-O⁶-diphenylcarbamoyl-N²-phenylacetyl-2'-deoxyguanosin-3'-yl methyl boranophosphate
  参考文献：
  名称：

  A Novel Method for the Synthesis of Dinucleoside Boranophosphates by a Boranophosphotriester Method

  摘要：

  2'-Deoxyribonucleoside-3'-boranophosphates (nucleotide monomers), including four kinds of nucleobases, were synthesized in good yields by the use of new boranophosphorylating reagents. We have explored various kinds of condensing reagents as well as nucleophilic catalysts for the boranophosphorylation reaction with nucleosides. In the synthesis of dinucleoside boranophosphates, undesirable side reactions occurred at the O-4 of thymine and the O-6 of N-2-phenylacetylguanine bases. To avoid these side reactions, additional protecting groups, benzoyl (Bz) and diphenylcarbamoyl (Dpc) groups, were introduced to thymine and guanine bases, respectively. As a result, the condensation reactions proceeded smoothly without any side reactions, and the dimers including four kinds of nucleobases were obtained in excellent yields. In the deprotection of the 5'-DMTr group, Et3SiH was found to be effective as a scavenger for the DMTr cation which caused a P-B bond cleavage. After removal of the other protecting groups by the conventional procedure, four kinds of dinucleoside boranophosphates were obtained in good yields.

  DOI：

  10.1021/jo0493875
• 作为产物：
  描述：

  二苯氨基甲酰氯 在 吡啶 、 六甲基二硅氮烷 作用下， 以 乙腈 为溶剂， 反应 22.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-O6-diphenylcarbamoyl-N2-phenylacetyl-2'-deoxyguanosine
  参考文献：
  名称：

  A Novel Method for the Synthesis of Dinucleoside Boranophosphates by a Boranophosphotriester Method

  摘要：

  2'-Deoxyribonucleoside-3'-boranophosphates (nucleotide monomers), including four kinds of nucleobases, were synthesized in good yields by the use of new boranophosphorylating reagents. We have explored various kinds of condensing reagents as well as nucleophilic catalysts for the boranophosphorylation reaction with nucleosides. In the synthesis of dinucleoside boranophosphates, undesirable side reactions occurred at the O-4 of thymine and the O-6 of N-2-phenylacetylguanine bases. To avoid these side reactions, additional protecting groups, benzoyl (Bz) and diphenylcarbamoyl (Dpc) groups, were introduced to thymine and guanine bases, respectively. As a result, the condensation reactions proceeded smoothly without any side reactions, and the dimers including four kinds of nucleobases were obtained in excellent yields. In the deprotection of the 5'-DMTr group, Et3SiH was found to be effective as a scavenger for the DMTr cation which caused a P-B bond cleavage. After removal of the other protecting groups by the conventional procedure, four kinds of dinucleoside boranophosphates were obtained in good yields.

  DOI：

  10.1021/jo0493875

文献信息

• Solid-phase Synthesis of Oligodeoxyribonucleoside Boranophosphates by the Boranophosphotriester Method
  作者：Mamoru Shimizu、Kazuhiko Saigo、Takeshi Wada

  DOI：10.1021/jo0603779

  日期：2006.5.1

  the condensation reaction without causing β-elimination of the CE groups from the boranophosphate triesters. The internucleotidic CE groups were selectively removed by treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) under anhydrous conditions. The acetylation of the terminal 5‘-hydroxy group was found to be effective to suppress the decomposition of the BH3−ODNs during the DBU treatment on the

  通过固相硼三磷酸酯方法合成了含有四种核碱基的低聚脱氧核糖核苷硼酸磷酸酯（BH 3 -ODNs）。具有2-氰基乙基（CE）基团作为磷保护基的2'-脱氧核糖核苷3'-硼酸磷酸酯单体以高收率合成。发现了一种新的缩合试剂1,6-二甲基-2-（3-硝基-1,2,4-三唑-1-基）-2-吡咯烷-1-基-1,3,2-二氮杂磷鎓六氟磷酸盐对在固体载体上的缩合反应非常有效。我们还发现1,8-bis（N，N-二甲基氨基）萘可以加速缩合反应，而不会引起硼酸磷酸三酯中CE基团的β-消除。通过在无水条件下用1，8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）处理来选择性除去核苷酸间CE基团。发现末端5'-羟基的乙酰化有效地抑制了在固体载体上的DBU处理期间BH 3 -ODN的分解。在固相合成和脱保护反应的最佳条件下，以良好的收率合成了含有四种核碱基的BH 3 -ODNs（4聚体和12聚体）。BH 3的杂交特性通