(+)-5-methyl-1-((2R,4S,5R)-4-((triisopropylsilyl)oxy)-5-(((triisopropyl-silyl)oxy)methyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)dione | 54925-58-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: (+)-5-methyl-1-((2R,4S,5R)-4-((triisopropylsilyl)oxy)-5-(((triisopropyl-silyl)oxy)methyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)dione
• 英文别名: 3',5'-bis-O-(triisopropylsilyl)thymidine；3',5'-bis-O-TIPS-D-thymidine；O^3'_,O5'-bis-triisopropylsilanyl-thymidine；5-methyl-1-[(2R,4S,5R)-4-tri(propan-2-yl)silyloxy-5-[tri(propan-2-yl)silyloxymethyl]oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 54925-58-5
• 化学式: C₂₈H₅₄N₂O₅Si₂
• 分子量: 554.918
• InChiKey: VISLIJJDZMIJOL-JIMJEQGWSA-N

物化性质

• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.89
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-5-methyl-1-((2R,4S,5R)-4-((triisopropylsilyl)oxy)-5-(((triisopropyl-silyl)oxy)methyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)dione 在 咪唑 、 硫酸氢铵 、 sodium tetrahydroborate 、 碘 、 叔丁基锂 、 四丁基碘化铵 、 三苯基膦 、 六甲基二硅氮烷 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 、 正戊烷 为溶剂， 反应 21.83h， 生成 5-(hydroxymethyl)-1-(((4S,5R)-4-(triisopropylsilyloxy)-5-((triisopropylsilyloxy)methyl)-4,5-dihydrofuran-2-yl)methyl)-1H-pyrrole-2-carbaldehyde
  参考文献：
  名称：

  Stereoselective Synthesis of Acortatarins A and B

  摘要：

  Acortatarins A and B have been synthesized via stereoselective spirocyclizations of glycals. Mercury-mediated spirocyclization of a pyrrole monoalcohol side chain leads to acortatarin A. Glycal epoxidation and reductive spirocyclization of a pyrrole dialdehyde side chain leads to acortatarin B. Acid equilibration and crystallographic analysis indicate that acortatarin B is a contrathermodynamic spiroketal with distinct ring conformations compared to acortatarin A.

  DOI：

  10.1021/ol3019456
• 作为产物：
  描述：

  三异丙基氯硅烷 、 beta-胸苷 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以99%的产率得到(+)-5-methyl-1-((2R,4S,5R)-4-((triisopropylsilyl)oxy)-5-(((triisopropyl-silyl)oxy)methyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)dione
  参考文献：
  名称：

  Stereoselective Synthesis of Acortatarins A and B

  摘要：

  Acortatarins A and B have been synthesized via stereoselective spirocyclizations of glycals. Mercury-mediated spirocyclization of a pyrrole monoalcohol side chain leads to acortatarin A. Glycal epoxidation and reductive spirocyclization of a pyrrole dialdehyde side chain leads to acortatarin B. Acid equilibration and crystallographic analysis indicate that acortatarin B is a contrathermodynamic spiroketal with distinct ring conformations compared to acortatarin A.

  DOI：

  10.1021/ol3019456

文献信息

• Boron-containing nucleic acids. Synthesis of cyanoborane adducts of 2'-deoxynucleosides
  作者：Anup Sood、Barbara Ramsay Shaw、Bernard F. Spielvogel

  DOI：10.1021/ja00208a019

  日期：1989.12

  Cyanoborane adducts of 2'-deoxynucleosides, specifically 2'-deoxyguanosine-N7-cyanoborane, 2'-deoxyadenosine-N1-cyanoborane, 2'-deoxyinosine-N7-cyanoborane, and 2'-deoxycytidine-N3-cyanoborane, were prepared by an exchange reaction of triphenylphosphine-cyanoborane (Ph 3 PBH 2 CH) with 3',5'-O-protected nucleosides

  2'-脱氧核苷的氰硼烷加合物，特别是 2'-脱氧鸟苷-N7-氰基硼烷、2'-脱氧腺苷-N1-氰基硼烷、2'-脱氧肌苷-N7-氰基硼烷和 2'-脱氧胞苷-N3-氰基硼烷，由三苯基膦-氰基硼烷 (Ph 3 PBH 2 CH) 与 3',5'-O-保护的核苷的交换反应
• 1,3-DIPOLAR CYCLOADDITION REACTIONS OF 3′,5′-<i>BIS</i>-<i>O</i>-SILYL THYMIDINES. SYNTHESIS OF NOVEL AZABICYCLIC COMPOUNDS
  作者：G. Negrón、G. Calderón、F. Vázquez、L. Lomas、J. Cárdenas、C. Márquez、R. Gaviño

  DOI：10.1081/scc-120004847

  日期：2002.1

  An efficient one step procedure for the preparation of (4.3.0) bicyclic N-methylpyrrolidine thymidine derivatives 4, using cycloaddition reaction of the highly reactive non-stabilized azomethine ylide [Y] with 3',5'-Bis-O-silylthymidines 3.
• Stereoselective Synthesis of Acortatarins A and B
  作者：Jacqueline M. Wurst、Alyssa L. Verano、Derek S. Tan

  DOI：10.1021/ol3019456

  日期：2012.9.7

  Acortatarins A and B have been synthesized via stereoselective spirocyclizations of glycals. Mercury-mediated spirocyclization of a pyrrole monoalcohol side chain leads to acortatarin A. Glycal epoxidation and reductive spirocyclization of a pyrrole dialdehyde side chain leads to acortatarin B. Acid equilibration and crystallographic analysis indicate that acortatarin B is a contrathermodynamic spiroketal with distinct ring conformations compared to acortatarin A.