1-[(2R,3R,3aR,5S,7S,7aR)-3-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-5-((E)-styryl)-hexahydro-furo[3,2-b]pyran-2-yl]-1H-pyrimidine-2,4-dione | 212829-38-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(2R,3R,3aR,5S,7S,7aR)-3-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-5-((E)-styryl)-hexahydro-furo[3,2-b]pyran-2-yl]-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(2R,3R,3aR,5S,7S,7aR)-3-[tert-butyl(dimethyl)silyl]oxy-7-hydroxy-5-[(E)-2-phenylethenyl]-3,3a,5,6,7,7a-hexahydro-2H-furo[3,2-b]pyran-2-yl]pyrimidine-2,4-dione
• CAS: 212829-38-4
• 化学式: C₂₅H₃₄N₂O₆Si
• 分子量: 486.64
• InChiKey: HLQJQIPVWIPBKA-NLLKXGAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  97.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[(2R,3R,3aR,5S,7S,7aR)-3-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-5-((E)-styryl)-hexahydro-furo[3,2-b]pyran-2-yl]-1H-pyrimidine-2,4-dione 在 吡啶 、 18-冠醚-6 作用下， 以 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：

  Benzoic acid (2R,3R,3aS,5S,7S,7aR)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-5-((E)-styryl)-hexahydro-furo[3,2-b]pyran-7-yl ester 在 咪唑 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-[(2R,3R,3aR,5S,7S,7aR)-3-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-5-((E)-styryl)-hexahydro-furo[3,2-b]pyran-2-yl]-1H-pyrimidine-2,4-dione
  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.