Benzoic acid (1S,3S)-3-(tert-butyl-dimethyl-silanyloxy)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-(2-fluoro-pyridin-3-yl)-propyl ester | 148132-77-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzoic acid (1S,3S)-3-(tert-butyl-dimethyl-silanyloxy)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-(2-fluoro-pyridin-3-yl)-propyl ester
• CAS: 148132-77-8
• 化学式: C₂₆H₃₆FNO₅Si
• 分子量: 489.659
• InChiKey: HHUWJSLJIGJQON-FDFHNCONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.05
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  66.88
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Benzoic acid (1S,3S)-3-(tert-butyl-dimethyl-silanyloxy)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-(2-fluoro-pyridin-3-yl)-propyl ester 在 氢氧化钾 、 氨 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 2.0h， 生成 (2R,3S,5R)-5-(2-Benzyloxy-pyridin-3-yl)-2-hydroxymethyl-tetrahydro-furan-3-ol
  参考文献：
  名称：

  Stereocontrolled syntheses of C-linked deoxyribosides of 2-hydroxypyridine and 2-hydroxyquinoline

  摘要：

  2'-Deoxy-C-ribosides 4 and 5 were prepared in optically active form by a route expected to be generally useful for the synthesis of the alpha- or beta-anomers of 2'-deoxy-C-ribosides. Key steps are the addition of an organometallic reagent to aldehyde 7, mesylation of the resulting alcohol, and stereospecific deprotection/cyclization to yield the 2'-deoxy-C-riboside (7 + 8 --> 9/10; 9 --> 11).

  DOI：

  10.1016/s0040-4039(00)92690-x
• 作为产物：
  描述：

  1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 在 臭氧 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 生成 Benzoic acid (1S,3S)-3-(tert-butyl-dimethyl-silanyloxy)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-(2-fluoro-pyridin-3-yl)-propyl ester
  参考文献：
  名称：

  Stereocontrolled syntheses of C-linked deoxyribosides of 2-hydroxypyridine and 2-hydroxyquinoline

  摘要：

  2'-Deoxy-C-ribosides 4 and 5 were prepared in optically active form by a route expected to be generally useful for the synthesis of the alpha- or beta-anomers of 2'-deoxy-C-ribosides. Key steps are the addition of an organometallic reagent to aldehyde 7, mesylation of the resulting alcohol, and stereospecific deprotection/cyclization to yield the 2'-deoxy-C-riboside (7 + 8 --> 9/10; 9 --> 11).

  DOI：

  10.1016/s0040-4039(00)92690-x