[(2-tert-Butyldisulfanyl-ethoxycarbonylamino)-(6-hydroxy-hexylcarbamoyl)-methyl]-carbamic acid 2-tert-butyldisulfanyl-ethyl ester | 861659-93-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(2-tert-Butyldisulfanyl-ethoxycarbonylamino)-(6-hydroxy-hexylcarbamoyl)-methyl]-carbamic acid 2-tert-butyldisulfanyl-ethyl ester
• 英文别名: 2-(tert-butyldisulfanyl)ethyl N-[1-[2-(tert-butyldisulfanyl)ethoxycarbonylamino]-2-(6-hydroxyhexylamino)-2-oxoethyl]carbamate
• CAS: 861659-93-0
• 化学式: C₂₂H₄₃N₃O₆S₄
• 分子量: 573.864
• InChiKey: YOGUAZQVWMSQSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  35
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  227
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2-tert-Butyldisulfanyl-ethoxycarbonylamino)-(6-hydroxy-hexylcarbamoyl)-methyl]-carbamic acid 2-tert-butyldisulfanyl-ethyl ester 、 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 2.0h， 以47%的产率得到((2-tert-Butyldisulfanyl-ethoxycarbonylamino)-{6-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-hexylcarbamoyl}-methyl)-carbamic acid 2-tert-butyldisulfanyl-ethyl ester
  参考文献：
  名称：

  A novel phosphoramidite for the synthesis of α-oxo aldehyde-modified oligodeoxynucleotides

  摘要：

  The synthesis and use of a novel phosphoramiditederivatized by a bis[2-(tert-butyldisulfanyl)ethoxycarbonylamino]acetyl moiety for the synthesis of oligodeoxynucleotides modified at the 5'-end by an alpha-oxo aldehyde functionality is presented. Incorporation of the phosphoramidite reagent was performed after the automated solid-phase oligonucleotide synthesis. Simultaneous cleavage/deprotection of the oligodeoxynucleotides and unmasking of the alpha-oxo aldehyde group could be achieved using NaOH in aqueous methanol in the presence of dithiothreitol. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.144
• 作为产物：
  描述：

  2-(tert-butyldisulfanyl)ethanol 在 ammonium hydroxide 、 1-羟基苯并三唑 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 27.0h， 生成 [(2-tert-Butyldisulfanyl-ethoxycarbonylamino)-(6-hydroxy-hexylcarbamoyl)-methyl]-carbamic acid 2-tert-butyldisulfanyl-ethyl ester
  参考文献：
  名称：

  A novel phosphoramidite for the synthesis of α-oxo aldehyde-modified oligodeoxynucleotides

  摘要：

  The synthesis and use of a novel phosphoramiditederivatized by a bis[2-(tert-butyldisulfanyl)ethoxycarbonylamino]acetyl moiety for the synthesis of oligodeoxynucleotides modified at the 5'-end by an alpha-oxo aldehyde functionality is presented. Incorporation of the phosphoramidite reagent was performed after the automated solid-phase oligonucleotide synthesis. Simultaneous cleavage/deprotection of the oligodeoxynucleotides and unmasking of the alpha-oxo aldehyde group could be achieved using NaOH in aqueous methanol in the presence of dithiothreitol. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.144

文献信息

• A novel phosphoramidite for the synthesis of α-oxo aldehyde-modified oligodeoxynucleotides
  作者：Samia Far、Catherine Gouyette、Oleg Melnyk

  DOI：10.1016/j.tet.2005.03.144

  日期：2005.6

  The synthesis and use of a novel phosphoramiditederivatized by a bis[2-(tert-butyldisulfanyl)ethoxycarbonylamino]acetyl moiety for the synthesis of oligodeoxynucleotides modified at the 5'-end by an alpha-oxo aldehyde functionality is presented. Incorporation of the phosphoramidite reagent was performed after the automated solid-phase oligonucleotide synthesis. Simultaneous cleavage/deprotection of the oligodeoxynucleotides and unmasking of the alpha-oxo aldehyde group could be achieved using NaOH in aqueous methanol in the presence of dithiothreitol. (c) 2005 Elsevier Ltd. All rights reserved.