5'-O-benzoyl-2',3'-bis-O-(tertbutyldimethylsilyl)-5'-phenylselenouridine | 161867-34-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5'-O-benzoyl-2',3'-bis-O-(tertbutyldimethylsilyl)-5'-phenylselenouridine
• 英文别名: [[(2S,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]-phenylselanylmethyl] benzoate
• CAS: 161867-34-1
• 化学式: C₃₄H₄₈N₂O₇SeSi₂
• 分子量: 731.895
• InChiKey: NJJJLDGVMYFXAY-RZGMYJSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  46
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-1-phenyl-(2-tributylstannyl)ethene 、 5'-O-benzoyl-2',3'-bis-O-(tertbutyldimethylsilyl)-5'-phenylselenouridine 在 六正丁基二锡 作用下， 以 苯 为溶剂， 生成 [(E,1S)-1-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]-3-phenylprop-2-enyl] benzoate
  参考文献：
  名称：

  The synthesis of octosyl nucleosides based on intramolecular oxyselenation of a conjugated diene

  摘要：

  A new stereoselective ring construction for 3,7-anhydrooctofuranosyl nucleoside, which is based on a 6-endo-trig oxyselenation of a conjugate diene, (5'S)-C-(4-phenyl-1,3-butadienyl)uridine, was developed. Because of the appropriate array of Functionalities at the 5', 6', and 7'-positions, the cyclization product 14 can be considered to be a versatile synthon for the synthesis of a series of octosyl nucleoside antibiotics. Factors governing the efficiency of this cyclization are also discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01087-9
• 作为产物：
  描述：

  2',3'-bis-O-(tert-butyldimethylsilyl)-5'-deoxy-5'-(phenylseleno)uridine 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 5'-O-benzoyl-2',3'-bis-O-(tertbutyldimethylsilyl)-5'-phenylselenouridine
  参考文献：
  名称：

  尿苷5'-单硒缩醛作为非对映选择性均溶CC键形成的底物

  摘要：

  通过5'-脱氧-5'-苯基硒代尿苷的硒化-Pummerer反应制备的尿苷5'-单硒缩醛用作与烯丙基三丁基锡进行自由基介导的反应的底物。2'，3'-O-异亚丙基衍生物的反应生成环化产物5-烯丙基-6,5'-环核苷，而2'，3'-双-O-（叔丁基二甲基甲硅烷基衍生物的那些则经历了CC键在5'-位形成（5'S）-和（5'R）-异构体，讨论了两种反应的立体化学结果，还研究了烯丙基三丁基锡以外的自由基受体的使用。

  DOI：

  10.1016/0040-4020(96)00483-8

文献信息

• Diastereoface selectivity in radical-mediated C-C bond formation of uridine 5′-monoselenoacetals
  作者：Kazuhiro Haraguchi、Hiromichi Tanaka、Shigeru Saito、Kentaro Yamaguchi、Tadashi Miyasaka

  DOI：10.1016/0040-4039(94)88369-6

  日期：1994.12

  Intramolecular radical reaction of 2′,3′-O-isopropylideneuridine 5′-monoselenoacetal 6 appeared to result in reverse stereoselectivity to that of the corresponding 5′-aldehyde (3). Intermolecular version of this reaction by using allyltributylstannane as a radical acceptor showed preferential anti-Cram diastereoface selection.

  2'，3'-O-异亚丙基亚尿苷5'-单硒缩醛6的分子内自由基反应似乎导致与相应的5'-醛（3）相反的立体选择性。该反应的分子间形式通过使用烯丙基三丁基锡烷作为自由基受体显示出优先的抗Cram非对映体选择。
• The synthesis of octosyl nucleosides based on intramolecular oxyselenation of a conjugated diene
  作者：Kazuhiro Haraguchi、Motoi Hosoe、Hiromichi Tanaka、Sayo Tsuruoka、Kazuhiro Kanmuri、Tadashi Miyasaka

  DOI：10.1016/s0040-4039(98)01087-9

  日期：1998.7

  A new stereoselective ring construction for 3,7-anhydrooctofuranosyl nucleoside, which is based on a 6-endo-trig oxyselenation of a conjugate diene, (5'S)-C-(4-phenyl-1,3-butadienyl)uridine, was developed. Because of the appropriate array of Functionalities at the 5', 6', and 7'-positions, the cyclization product 14 can be considered to be a versatile synthon for the synthesis of a series of octosyl nucleoside antibiotics. Factors governing the efficiency of this cyclization are also discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Uridine 5′-monoselenoacetals as substrates for diastereoselective homolytic C-C bond formation
  作者：Kazuhiro Haraguchi、Hiromichi Tanaka、Shigeru Saito、Satomi Kinoshima、Motoi Hosoe、Kazuhiro Kanmuri、Kentaro Yamaguchi、Tadashi Miyasaka

  DOI：10.1016/0040-4020(96)00483-8

  日期：1996.7

  Uridine 5′-monoselenoacetals prepared by the seleno-Pummerer reaction of 5′-deoxy-5′-phenylseleno-uridines were used as substrates for radical-mediated reactions with allyltributyltin. The reaction of the 2′,3′-O-isopropylidene derivative gave cyclized products, 5-allyl-6,5′-cyclonucleosides, whereas those of the 2′,3′-bis-O-(tertbutyldimethylsilyl derivatives underwent the C-C bond formation at the

  通过5'-脱氧-5'-苯基硒代尿苷的硒化-Pummerer反应制备的尿苷5'-单硒缩醛用作与烯丙基三丁基锡进行自由基介导的反应的底物。2'，3'-O-异亚丙基衍生物的反应生成环化产物5-烯丙基-6,5'-环核苷，而2'，3'-双-O-（叔丁基二甲基甲硅烷基衍生物的那些则经历了CC键在5'-位形成（5'S）-和（5'R）-异构体，讨论了两种反应的立体化学结果，还研究了烯丙基三丁基锡以外的自由基受体的使用。