6-monomethoxytrityloxy-6'-hydroxy-bis-(hexanoylhydrazinocarbonyl-2-oxyethyl)sulfone | 873694-56-5

• 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: 6-monomethoxytrityloxy-6'-hydroxy-bis-(hexanoylhydrazinocarbonyl-2-oxyethyl)sulfone
• CAS: 873694-56-5
• 化学式: C₃₈H₅₀N₄O₁₁S
• 分子量: 770.901
• InChiKey: RDVYABKCWNTNTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  54.0
• 可旋转键数：
  22.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  207.69
• 氢给体数：
  5.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  6-monomethoxytrityloxy-6'-hydroxy-bis-(hexanoylhydrazinocarbonyl-2-oxyethyl)sulfone 、 双(二异丙基氨基)(2-氰基乙氧基)膦 在 diisopropylamidotetrazolide 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 6-monomethoxytrityloxy-6'-[(2-cyanoethoxy)(diisopropylamino)phosphanyloxy]-bis-(hexanoylhydrazinocarbonyl-2-oxyethyl)sulfone
  参考文献：
  名称：

  A Novel Versatile Phosphoramidite Building Block for the Synthesis of 5'- and 3'-Hydrazide Modified Oligonucleotides

  摘要：

  We introduce a novel versatile phosphoramidite building block for the modification of oligonucleotides (ONs) with acyl hydrazides on the 5'- or 3'-terminus, or both. The reaction of these hydrazide functionalized ONs with 4-methoxyphenylaldehyde is demonstrated for solution derivatization. Hydrazides are considered nowadays as promising reactants, which show enhanced reactivity at neutral and slightly acidic conditions and higher stability of yielding products as compared to the aliphatic amines, which are broadly used for ONs derivatization.Our method to introduce hydrazides into ONs employs a phosphoramidite modifier designed to split, during ammonia or lithium hydroxide treatment, into two hydrazides via beta-elimination of a central bis-2-carbonylethoxysulfone unit. It allows the creation of ONs derivatized with a hydrazide moiety at the 5'-, 3'- and both 5- and 3'-termini, as well as two different hydrazide containing ONs at the same time, viz. in one sequence on the same solid support. In latter case one can, for example, synthesize two hydrazide containing ONs, where one is 5'-modified and second one is 3'-modified.

  DOI：

  10.1081/ncn-200055723
• 作为产物：
  描述：

  bis-[(4-nitrophenyl)oxycarbonyl-2-oxyethyl]sulfone 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 6-monomethoxytrityloxy-6'-hydroxy-bis-(hexanoylhydrazinocarbonyl-2-oxyethyl)sulfone
  参考文献：
  名称：

  A Novel Versatile Phosphoramidite Building Block for the Synthesis of 5'- and 3'-Hydrazide Modified Oligonucleotides

  摘要：

  We introduce a novel versatile phosphoramidite building block for the modification of oligonucleotides (ONs) with acyl hydrazides on the 5'- or 3'-terminus, or both. The reaction of these hydrazide functionalized ONs with 4-methoxyphenylaldehyde is demonstrated for solution derivatization. Hydrazides are considered nowadays as promising reactants, which show enhanced reactivity at neutral and slightly acidic conditions and higher stability of yielding products as compared to the aliphatic amines, which are broadly used for ONs derivatization.Our method to introduce hydrazides into ONs employs a phosphoramidite modifier designed to split, during ammonia or lithium hydroxide treatment, into two hydrazides via beta-elimination of a central bis-2-carbonylethoxysulfone unit. It allows the creation of ONs derivatized with a hydrazide moiety at the 5'-, 3'- and both 5- and 3'-termini, as well as two different hydrazide containing ONs at the same time, viz. in one sequence on the same solid support. In latter case one can, for example, synthesize two hydrazide containing ONs, where one is 5'-modified and second one is 3'-modified.

  DOI：

  10.1081/ncn-200055723