(R)-2-[N-(6'-hydroxyhexyl)carbamoyl]oxy-1-(4-monomethoxytrityl)amino-3-(1-naphthylmethoxy)propane | 922522-02-9

• 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: (R)-2-[N-(6'-hydroxyhexyl)carbamoyl]oxy-1-(4-monomethoxytrityl)amino-3-(1-naphthylmethoxy)propane
• CAS: 922522-02-9
• 化学式: C₄₁H₄₆N₂O₅
• 分子量: 646.827
• InChiKey: OMYFFZQZXIMBAJ-KXQOOQHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.59
• 重原子数：
  48.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  89.05
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-2-[N-(6'-hydroxyhexyl)carbamoyl]oxy-1-(4-monomethoxytrityl)amino-3-(1-naphthylmethoxy)propane 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以73%的产率得到(R)-2-[N-(6'-hydroxyhexyl)carbamoyl]oxy-1-(4-monomethoxytrityl)amino-3-(1-naphthylmethoxy)propane 6'-O-(2-cyanoethyl-N,N-diisopropylphosphoramidite)
  参考文献：
  名称：

  Novel amino linkers enabling efficient labeling and convenient purification of amino-modified oligonucleotides

  摘要：

  We developed new amino linker reagents for an oligonucleotide (ONT) terminus. These reagents consist of an aminoethyl carbamate main linkage and a side-chain residue, which was a naphthylmethoxymethyl, methoxymethyl, or methyl group or a hydrogen atom. The primary amine was protected with a monomethoxytrityl (MMT) group. The chemical properties of ONTs containing these amino-modifications were investigated. The MMT group of these amino-modifications could be quite rapidly removed from the amine under very mild acidic conditions, which are not strong enough for the deprotection of a conventional aliphatic amine. This significant feature enabled the amino-modified ONTs to be conveniently purified with a reverse phase column. Furthermore, the amino-modifications efficiently reacted to active esters, as compared with other amino-modifications. We also found that the pK(a), values of the amino-modifications were lower than that of the aliphatic amine. All of the experimental results showed that these chemical properties are closely related to their structures. We report here the chemical properties and the availability of the new amino linker reagents. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.011
• 作为产物：
  描述：

  (R)-1-(4-monomethoxytrityl)amino-3-(1-naphthylmethoxy)propan-2-ol 、 6-氨基-1-己醇 、 N,N'-羰基二咪唑 在 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 以92%的产率得到(R)-2-[N-(6'-hydroxyhexyl)carbamoyl]oxy-1-(4-monomethoxytrityl)amino-3-(1-naphthylmethoxy)propane
  参考文献：
  名称：

  Novel amino linkers enabling efficient labeling and convenient purification of amino-modified oligonucleotides

  摘要：

  We developed new amino linker reagents for an oligonucleotide (ONT) terminus. These reagents consist of an aminoethyl carbamate main linkage and a side-chain residue, which was a naphthylmethoxymethyl, methoxymethyl, or methyl group or a hydrogen atom. The primary amine was protected with a monomethoxytrityl (MMT) group. The chemical properties of ONTs containing these amino-modifications were investigated. The MMT group of these amino-modifications could be quite rapidly removed from the amine under very mild acidic conditions, which are not strong enough for the deprotection of a conventional aliphatic amine. This significant feature enabled the amino-modified ONTs to be conveniently purified with a reverse phase column. Furthermore, the amino-modifications efficiently reacted to active esters, as compared with other amino-modifications. We also found that the pK(a), values of the amino-modifications were lower than that of the aliphatic amine. All of the experimental results showed that these chemical properties are closely related to their structures. We report here the chemical properties and the availability of the new amino linker reagents. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.011