trimethyl-[2-[5-methyl-2-[[(2S)-5-phenylselanyloxolan-2-yl]methoxy]pyrimidin-4-yl]oxyethyl]silane | 204636-97-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trimethyl-[2-[5-methyl-2-[[(2S)-5-phenylselanyloxolan-2-yl]methoxy]pyrimidin-4-yl]oxyethyl]silane
• CAS: 204636-97-5
• 化学式: C₂₁H₃₀N₂O₃SeSi
• 分子量: 465.526
• InChiKey: YKRZQUADMBRSJA-KKFHFHRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  53.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  trimethyl-[2-[5-methyl-2-[[(2S)-5-phenylselanyloxolan-2-yl]methoxy]pyrimidin-4-yl]oxyethyl]silane 在 sodium hydroxide 、 四丁基氟化铵 、 silver trifluoromethanesulfonate 作用下， 生成 2',3'-二脱氧胸苷
  参考文献：
  名称：

  Stereoselective synthesis of 2′,3′-dideoxy-nucleosides via intramolecular glycosylation of phenyl 1-seleno-glycosides. Synthesis of 2′,3′-dideoxythymidine

  摘要：

  4-methoxy and 4-(2-trimethylsilylethoxy)pyrimidine bases were attached to the 5-position of the phenyl 2,3-dideoxy-1-seleno-glycero-pentofuranoside moiety. The presence of the silyl protecting group in the base is necessary to lend to neutral beta-anhydro nucleosides by intramolecular glycosylation. The subsequent ring opening affords 3'-deoxythymidine with complete stereocontrol. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00093-8
• 作为产物：
  描述：

  2,4-二氯-5-甲基嘧啶 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 生成 trimethyl-[2-[5-methyl-2-[[(2S)-5-phenylselanyloxolan-2-yl]methoxy]pyrimidin-4-yl]oxyethyl]silane
  参考文献：
  名称：

  Stereoselective synthesis of 2′,3′-dideoxy-nucleosides via intramolecular glycosylation of phenyl 1-seleno-glycosides. Synthesis of 2′,3′-dideoxythymidine

  摘要：

  4-methoxy and 4-(2-trimethylsilylethoxy)pyrimidine bases were attached to the 5-position of the phenyl 2,3-dideoxy-1-seleno-glycero-pentofuranoside moiety. The presence of the silyl protecting group in the base is necessary to lend to neutral beta-anhydro nucleosides by intramolecular glycosylation. The subsequent ring opening affords 3'-deoxythymidine with complete stereocontrol. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00093-8

文献信息

• Stereoselective synthesis of 2′,3′-dideoxy-nucleosides via intramolecular glycosylation of phenyl 1-seleno-glycosides. Synthesis of 2′,3′-dideoxythymidine
  作者：Jordi Lluís、MaIsabel Matheu、Sergio Castillón

  DOI：10.1016/s0040-4039(98)00093-8

  日期：1998.3

  4-methoxy and 4-(2-trimethylsilylethoxy)pyrimidine bases were attached to the 5-position of the phenyl 2,3-dideoxy-1-seleno-glycero-pentofuranoside moiety. The presence of the silyl protecting group in the base is necessary to lend to neutral beta-anhydro nucleosides by intramolecular glycosylation. The subsequent ring opening affords 3'-deoxythymidine with complete stereocontrol. (C) 1998 Elsevier Science Ltd. All rights reserved.