(1R,5R,6S,8R)-3,3-dimethyl-6-(p-trifluoroacetylaminophenyl)-6-(2'-propenyl)-8-(tert-butyldiphenylsilyloxymethyl)-2,4,7-trioxabicyclo[3.3.0]octane | 1050206-92-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,5R,6S,8R)-3,3-dimethyl-6-(p-trifluoroacetylaminophenyl)-6-(2'-propenyl)-8-(tert-butyldiphenylsilyloxymethyl)-2,4,7-trioxabicyclo[3.3.0]octane
• 英文别名: N-[4-[(3aR,4S,6R,6aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-4-prop-2-enyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]phenyl]-2,2,2-trifluoroacetamide
• CAS: 1050206-92-2
• 化学式: C₃₅H₄₀F₃NO₅Si
• 分子量: 639.787
• InChiKey: HDQNYQZQRLXBTK-JCUDBWTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.45
• 重原子数：
  45
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1R,5R,6S,8R)-3,3-dimethyl-6-(p-trifluoroacetylaminophenyl)-6-(2'-propenyl)-8-(tert-butyldiphenylsilyloxymethyl)-2,4,7-trioxabicyclo[3.3.0]octane 、 乙酸酐 、 三氟乙酸酐 在 吡啶 、 sodium periodate 、 四氧化锇 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到(1R,3R,4R,5R)-1-(p-trifluoroacetylaminophenyl)-3-(tert-butyldiphenylsilyloxymethyl)-4,7-diacetoxy-2,6-dioxabicyclo[3.3.0]octane
  参考文献：
  名称：

  Synthesis of p-amino-WNA derivatives to enhance the stability of the anti-parallel triplex

  摘要：

  We have previously developed W-shaped nucleoside analogs (WNAs) having a nucleobase and an aromatic ring for the formation of the unnatural triplex DNA. Modification of an aromatic ring of WNA is highly effective regarding the stability of the triplex DNA. In this study, we designed new WNA analogs having the p-aminobenzene as an aromatic ring, which were synthesized via the Curtius-Yamada rearrangement. Based on the evaluation of the triplex formation with p-amino-WNA-TFO, it has been shown that the amino group may produce a non-selective interaction with the phosphate backbone of the target duplexes. These results indicate that the amino modification is useful to overcome the sequence-dependence of the TFO containing WNA analogs. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.096
• 作为产物：
  描述：

  、 三氟乙酸酐 在 吡啶 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 91.5h， 以5.16 g的产率得到(1R,5R,6S,8R)-3,3-dimethyl-6-(p-trifluoroacetylaminophenyl)-6-(2'-propenyl)-8-(tert-butyldiphenylsilyloxymethyl)-2,4,7-trioxabicyclo[3.3.0]octane
  参考文献：
  名称：

  Synthesis of p-amino-WNA derivatives to enhance the stability of the anti-parallel triplex

  摘要：

  We have previously developed W-shaped nucleoside analogs (WNAs) having a nucleobase and an aromatic ring for the formation of the unnatural triplex DNA. Modification of an aromatic ring of WNA is highly effective regarding the stability of the triplex DNA. In this study, we designed new WNA analogs having the p-aminobenzene as an aromatic ring, which were synthesized via the Curtius-Yamada rearrangement. Based on the evaluation of the triplex formation with p-amino-WNA-TFO, it has been shown that the amino group may produce a non-selective interaction with the phosphate backbone of the target duplexes. These results indicate that the amino modification is useful to overcome the sequence-dependence of the TFO containing WNA analogs. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.096

文献信息

• Synthesis of p-amino-WNA derivatives to enhance the stability of the anti-parallel triplex
  作者：Yosuke Taniguchi、Mieko Togo、Eriko Aoki、Yuko Uchida、Shigeki Sasaki

  DOI：10.1016/j.tet.2008.05.096

  日期：2008.7

  We have previously developed W-shaped nucleoside analogs (WNAs) having a nucleobase and an aromatic ring for the formation of the unnatural triplex DNA. Modification of an aromatic ring of WNA is highly effective regarding the stability of the triplex DNA. In this study, we designed new WNA analogs having the p-aminobenzene as an aromatic ring, which were synthesized via the Curtius-Yamada rearrangement. Based on the evaluation of the triplex formation with p-amino-WNA-TFO, it has been shown that the amino group may produce a non-selective interaction with the phosphate backbone of the target duplexes. These results indicate that the amino modification is useful to overcome the sequence-dependence of the TFO containing WNA analogs. (c) 2008 Elsevier Ltd. All rights reserved.