[(2R,3S,4R,5R,6S)-4,5,6-tribenzoyloxy-3-(trifluoromethylsulfonyloxy)oxan-2-yl]methyl benzoate | 1228019-10-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(2R,3S,4R,5R,6S)-4,5,6-tribenzoyloxy-3-(trifluoromethylsulfonyloxy)oxan-2-yl]methyl benzoate
• CAS: 1228019-10-0
• 化学式: C₃₅H₂₇F₃O₁₂S
• 分子量: 728.653
• InChiKey: UMZBUTLMIMAIET-NFUQQPFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  51
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  166
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4R,5R,6S)-4,5,6-tribenzoyloxy-3-(trifluoromethylsulfonyloxy)oxan-2-yl]methyl benzoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 2-甲基四氢呋喃 为溶剂， 反应 2.0h， 以4.1%的产率得到1,2,3,6-tetra-O-benzoyl-4-fluoro-β-glucopyranoside
  参考文献：
  名称：

  Syntheses and NMR characterizations of epimeric 4-deoxy-4-fluoro carbohydrates

  摘要：

  The synthesis and NMR characterizations of 1,2,3,6-tetra-O-benzoyl-4-deoxy-4-fluoro-beta-D-galactopyranoside, the 4-deoxy-4-fluoro epimer of an intermediate in the synthesis of a drug substance, needed for use as a potential impurity standard and to confirm the stereoselectivity of a key fluorination step, are described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.07.019
• 作为产物：
  描述：

  三氟甲磺酸酐 、 1,2,3,6-tetra-O-benzoyl-β-D-galactopyranose 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 [(2R,3S,4R,5R,6S)-4,5,6-tribenzoyloxy-3-(trifluoromethylsulfonyloxy)oxan-2-yl]methyl benzoate
  参考文献：
  名称：

  Syntheses and NMR characterizations of epimeric 4-deoxy-4-fluoro carbohydrates

  摘要：

  The synthesis and NMR characterizations of 1,2,3,6-tetra-O-benzoyl-4-deoxy-4-fluoro-beta-D-galactopyranoside, the 4-deoxy-4-fluoro epimer of an intermediate in the synthesis of a drug substance, needed for use as a potential impurity standard and to confirm the stereoselectivity of a key fluorination step, are described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.07.019

文献信息

• Syntheses and NMR characterizations of epimeric 4-deoxy-4-fluoro carbohydrates
  作者：Witold Subotkowski、Dirk Friedrich、Franz J. Weiberth

  DOI：10.1016/j.carres.2011.07.019

  日期：2011.11

  The synthesis and NMR characterizations of 1,2,3,6-tetra-O-benzoyl-4-deoxy-4-fluoro-beta-D-galactopyranoside, the 4-deoxy-4-fluoro epimer of an intermediate in the synthesis of a drug substance, needed for use as a potential impurity standard and to confirm the stereoselectivity of a key fluorination step, are described. (C) 2011 Elsevier Ltd. All rights reserved.