2,2,2-Trifluoro-acetimidic acid (E)-3-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-allyl ester | 262601-74-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 2,2,2-Trifluoro-acetimidic acid (E)-3-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-allyl ester
• CAS: 262601-74-1
• 化学式: C₁₆H₂₂F₃NO₆
• 分子量: 381.349
• InChiKey: QEMRIFKESIDHHZ-QUBIXGNXSA-N

物化性质

• 沸点：
  367.6±52.0 °C(predicted)
• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  79.23
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2,2,2-Trifluoro-acetimidic acid (E)-3-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-allyl ester 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 xylene 为溶剂， 反应 50.0h， 生成
  参考文献：
  名称：

  Stereocontrolled introduction of an amino group at C-6 of d-galactose via (3,3)-sigmatropic rearrangements—novel synthesis of lincosamine and 7-epi-lincosamine precursors

  摘要：

  A new and stereoselective route to the aminoglycoside components of the antibiotics lincomycin and clindamycin is presented, The key step involves diastereoselective introduction of the amino group at C-6 of D-galactose by (3,3)-sigmatropic rearrangements of the corresponding allylic (Z)-trifluoroacetimidate and (Z)- and (E)-allylic thiocyanates. Epoxidation of the resulting trifluoroacetamide with m-CPBA led to the epoxide with high threo-selectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02110-3
• 作为产物：
  描述：

  methyl (Z)-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-oct-6-enopyranuronate 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 乙醚 为溶剂， 生成 2,2,2-Trifluoro-acetimidic acid (E)-3-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-allyl ester
  参考文献：
  名称：

  Stereocontrolled introduction of an amino group at C-6 of d-galactose via (3,3)-sigmatropic rearrangements—novel synthesis of lincosamine and 7-epi-lincosamine precursors

  摘要：

  A new and stereoselective route to the aminoglycoside components of the antibiotics lincomycin and clindamycin is presented, The key step involves diastereoselective introduction of the amino group at C-6 of D-galactose by (3,3)-sigmatropic rearrangements of the corresponding allylic (Z)-trifluoroacetimidate and (Z)- and (E)-allylic thiocyanates. Epoxidation of the resulting trifluoroacetamide with m-CPBA led to the epoxide with high threo-selectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02110-3