Oxalic acid (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-trifluoromethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester methyl ester | 1053625-95-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Oxalic acid (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-trifluoromethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester methyl ester
• 英文别名: 2-O-[(3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-(trifluoromethyl)-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-6-yl] 1-O-methyl oxalate
• CAS: 1053625-95-8
• 化学式: C₁₆H₂₁F₃O₉
• 分子量: 414.333
• InChiKey: HYNKKRFXDVKXMA-DLOBIDMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Oxalic acid (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-trifluoromethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester methyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 3-Deoxy-1,2:5,6-di-O-isopropylidene-3-C-trifluoromethyl-α-D-glucofuranose 、 3-Deoxy-1,2:5,6-di-O-isopropylidene-3-C-trifluoromethyl-α-D-allofuranose
  参考文献：
  名称：

  Synthesis of 3-Deoxy-3-C-Trifluoromethyl-d-Ribose Fromd-Xylose ord-Glucose

  摘要：

  The synthesis of 3-deoxy-1,2-O-isopropylidene-3-C-trifluoromethyl-alpha-D-ribofuranose is described. After a first approach from a commercial D-xylose derivative which was limited by an incomplete stereoselectivity, the synthesis of the title compound was performed from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose by a reaction sequence where key steps: trifluoromethylation with CF(3)SiMe(3) and radical deoxygenation are highly stereoselective.

  DOI：

  10.1080/07328309608005659
• 作为产物：
  描述：

  1,2:5,6-二-o-异亚丙基-alpha-d-ribo-3-己呋喃核糖 在 吡啶 、 甲醇 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 Oxalic acid (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-trifluoromethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester methyl ester
  参考文献：
  名称：

  Synthesis of 3-Deoxy-3-C-Trifluoromethyl-d-Ribose Fromd-Xylose ord-Glucose

  摘要：

  The synthesis of 3-deoxy-1,2-O-isopropylidene-3-C-trifluoromethyl-alpha-D-ribofuranose is described. After a first approach from a commercial D-xylose derivative which was limited by an incomplete stereoselectivity, the synthesis of the title compound was performed from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose by a reaction sequence where key steps: trifluoromethylation with CF(3)SiMe(3) and radical deoxygenation are highly stereoselective.

  DOI：

  10.1080/07328309608005659

文献信息

• Synthesis of 3-Deoxy-3-<i>C</i>-Trifluoromethyl-<scp>d</scp>-Ribose From<scp>d</scp>-Xylose or<scp>d</scp>-Glucose
  作者：S. Lavaire、R. Plantier-Royon、C. Portella

  DOI：10.1080/07328309608005659

  日期：1996.4

  The synthesis of 3-deoxy-1,2-O-isopropylidene-3-C-trifluoromethyl-alpha-D-ribofuranose is described. After a first approach from a commercial D-xylose derivative which was limited by an incomplete stereoselectivity, the synthesis of the title compound was performed from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose by a reaction sequence where key steps: trifluoromethylation with CF(3)SiMe(3) and radical deoxygenation are highly stereoselective.