(1R)-2-[tert-butyl(diphenyl)silyl]oxy-1-[(4R,5S)-5-[(S)-(3,5-dibromothiophen-2-yl)-hydroxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol | 1078144-09-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R)-2-[tert-butyl(diphenyl)silyl]oxy-1-[(4R,5S)-5-[(S)-(3,5-dibromothiophen-2-yl)-hydroxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol
• CAS: 1078144-09-8
• 化学式: C₂₈H₃₄Br₂O₅SSi
• 分子量: 670.534
• InChiKey: PLJCLTXENIFANY-WUEDSLEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  96.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R)-2-[tert-butyl(diphenyl)silyl]oxy-1-[(4R,5S)-5-[(S)-(3,5-dibromothiophen-2-yl)-hydroxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到
  参考文献：
  名称：

  A stereo- and regio-controlled synthesis of bromothiophenyl C-nucleosides. Tandem bromination-ribosylation via halogen dance process

  摘要：

  Metallation-ribosylation of 2-bromothiophene 1 when conducted at room temperature afforded the original glycosylated dibromothiophene 3b following a regiocontrolled halogen transfer-based halogen-dance process. Then, stereocontrolled reduction-cyclization of hemiacetals 3a-c allowed straightforward access to the halogenated thiophenyl-C-nucleosides 6a-c. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.071
• 作为产物：
  描述：

  (3aR,6R,6aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-(3,5-dibromothiophen-2-yl)-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-ol 在 L-Selectride 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以80%的产率得到(1R)-2-[tert-butyl(diphenyl)silyl]oxy-1-[(4R,5S)-5-[(S)-(3,5-dibromothiophen-2-yl)-hydroxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol
  参考文献：
  名称：

  A stereo- and regio-controlled synthesis of bromothiophenyl C-nucleosides. Tandem bromination-ribosylation via halogen dance process

  摘要：

  Metallation-ribosylation of 2-bromothiophene 1 when conducted at room temperature afforded the original glycosylated dibromothiophene 3b following a regiocontrolled halogen transfer-based halogen-dance process. Then, stereocontrolled reduction-cyclization of hemiacetals 3a-c allowed straightforward access to the halogenated thiophenyl-C-nucleosides 6a-c. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.071