2-[(1R,3R)-1-[(2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-3,4-dihydro-[1,3,2]oxazaphosphinino[3,4-a]indol-3-yl]acetonitrile | 252191-39-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 2-[(1R,3R)-1-[(2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-3,4-dihydro-[1,3,2]oxazaphosphinino[3,4-a]indol-3-yl]acetonitrile
• CAS: 252191-39-2
• 化学式: C₂₈H₃₇N₄O₆PSi
• 分子量: 584.684
• InChiKey: PFGHWNCQEZSCFT-NHWWCICZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(5-羟基戊基)异吲哚-1,3-二酮 、 2-[(1R,3R)-1-[(2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-3,4-dihydro-[1,3,2]oxazaphosphinino[3,4-a]indol-3-yl]acetonitrile 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 苯基二硫化物 作用下， 以 四氢呋喃 为溶剂， 生成 O-((2R,3S,5R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl) O-((R)-1-cyano-3-(1H-indol-2-yl)propan-2-yl) O-(5-(1,3-dioxoisoindolin-2-yl)pentyl) (R)-phosphorothioate
  参考文献：
  名称：

  Stereoselective synthesis of highly functionalised P-stereogenic nucleosides via palladium-catalysed P–C cross-coupling reactions

  摘要：

  We have shown that the configuration at the P-stereogenic centre in a range of H-phosphonates can be assigned using a combination of chromotographic mobility, (1)H and (31)P NMR data. We have also shown that the individual P-stereoisomers can be cross-coupled with vinyl and aryl halides, in the presence of a palladium(D) Catalyst, to afford the corresponding vinyl- and arylphosphonates in a stereocontrolled manner. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.102
• 作为产物：
  描述：

  (R)-3-hydroxy-4-(2-indolyl)butyronitrile 在 三乙胺 、 三氯化磷 作用下， 以 四氢呋喃 为溶剂， 生成 2-[(1R,3R)-1-[(2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-3,4-dihydro-[1,3,2]oxazaphosphinino[3,4-a]indol-3-yl]acetonitrile
  参考文献：
  名称：

  立体选择性合成二核苷酸硫代磷酸酯，使用手性吲哚-草氮杂磷中间体

  摘要：

  报道了使用（S）和（R）-3-羟基-4-（2-吲哚基）丁腈3b作为手性助剂的de＞ 98％的二核苷酸硫代磷酸酯的立体选择性合成。该程序可以适用于固相合成。

  DOI：

  10.1016/s0040-4039(97)00749-1

文献信息

• A stereoselective synthesis of dinucleotide phosphorothioates, using chiral indol-oxazaphosphorine intermediates
  作者：Jian-Chao Wang、George Just

  DOI：10.1016/s0040-4039(97)00749-1

  日期：1997.6

  A stereoselective synthesis of dinucleotide phosphorothioates with a de of > 98%, using (S) and (R)-3-hydroxy-4-(2-indolyl)butyronitrile 3b as chiral auxiliaries, is reported. The procedure may be adaptable to solid phase synthesis.

  报道了使用（S）和（R）-3-羟基-4-（2-吲哚基）丁腈3b作为手性助剂的de＞ 98％的二核苷酸硫代磷酸酯的立体选择性合成。该程序可以适用于固相合成。
• Stereoselective synthesis of highly functionalised P-stereogenic nucleosides via palladium-catalysed P–C cross-coupling reactions
  作者：Benjamin Whittaker、Manuel de Lera Ruiz、Christopher J. Hayes

  DOI：10.1016/j.tetlet.2008.09.102

  日期：2008.12

  We have shown that the configuration at the P-stereogenic centre in a range of H-phosphonates can be assigned using a combination of chromotographic mobility, (1)H and (31)P NMR data. We have also shown that the individual P-stereoisomers can be cross-coupled with vinyl and aryl halides, in the presence of a palladium(D) Catalyst, to afford the corresponding vinyl- and arylphosphonates in a stereocontrolled manner. (C) 2008 Elsevier Ltd. All rights reserved.