Benzoic acid (2R,3R,3aS,5R,6R,7R,7aS)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-6-phenylselanyl-5-((E)-styryl)-hexahydro-furo[3,2-b]pyran-7-yl ester | 212829-35-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzoic acid (2R,3R,3aS,5R,6R,7R,7aS)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-6-phenylselanyl-5-((E)-styryl)-hexahydro-furo[3,2-b]pyran-7-yl ester
• 英文别名: [(2R,3R,3aS,5R,6R,7R,7aS)-2-(2,4-dioxopyrimidin-1-yl)-3-hydroxy-5-[(E)-2-phenylethenyl]-6-phenylselanyl-3,3a,5,6,7,7a-hexahydro-2H-furo[3,2-b]pyran-7-yl] benzoate
• CAS: 212829-35-1
• 化学式: C₃₂H₂₈N₂O₇Se
• 分子量: 631.544
• InChiKey: JPXOJYCNESBVOX-SJUQNSNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2R,3R,3aS,5R,6R,7R,7aS)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-6-phenylselanyl-5-((E)-styryl)-hexahydro-furo[3,2-b]pyran-7-yl ester 在 吡啶 、 咪唑 、 18-冠醚-6 、 三乙基硼 、 四丁基氟化铵 、 氧气 、 三正丁基氢锡 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 生成 [(2R,3R,3aR,5S,7R,7aR)-3-[tert-butyl(dimethyl)silyl]oxy-2-(2,4-dioxopyrimidin-1-yl)-5-[(E)-2-phenylethenyl]-3,3a,5,6,7,7a-hexahydro-2H-furo[3,2-b]pyran-7-yl] acetate
  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：

  苯基氯化硒 、 Benzoic acid (2Z,4E)-(S)-1-[(2S,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-5-phenyl-penta-2,4-dienyl ester 以 二氯甲烷 、 乙腈 为溶剂， 以73%的产率得到Benzoic acid (2R,3R,3aS,5R,6R,7R,7aS)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-6-phenylselanyl-5-((E)-styryl)-hexahydro-furo[3,2-b]pyran-7-yl ester
  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

文献信息

• 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.