ethyl 2-[(2R,3S,6S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(2,2,2-trichloroethanimidoyl)oxy-3,6-dihydro-2H-pyran-6-yl]-2,2-difluoroacetate | 1149347-40-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: ethyl 2-[(2R,3S,6S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(2,2,2-trichloroethanimidoyl)oxy-3,6-dihydro-2H-pyran-6-yl]-2,2-difluoroacetate
• CAS: 1149347-40-9
• 化学式: C₂₈H₃₂Cl₃F₂NO₅Si
• 分子量: 635.007
• InChiKey: MYQFNRHWFRAEEI-ZRBLBEILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.82
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(2R,3S,6S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(2,2,2-trichloroethanimidoyl)oxy-3,6-dihydro-2H-pyran-6-yl]-2,2-difluoroacetate 以 邻二氯苯 为溶剂， 以32%的产率得到
  参考文献：
  名称：

  Approaches to the synthesis of CF2-analogues of 2-deoxy-2-aminoglycosides

  摘要：

  The preparation of a fluorinated C-glycosidic analogue of a 2-deoxy-2-acetamido-D-altrose is described. The synthetic sequence involves the addition of a difluoroenoxysilane to a D-glucal, an epoxidation of the resulting unsaturated CF2-glycoside and a ring-opening reaction with TMSN3. An Overman rearrangement of the unsaturated intermediate is also described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.155
• 作为产物：
  描述：

  ethyl 2-(6-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-2,2-difluoroacetate 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以86%的产率得到ethyl 2-[(2R,3S,6S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(2,2,2-trichloroethanimidoyl)oxy-3,6-dihydro-2H-pyran-6-yl]-2,2-difluoroacetate
  参考文献：
  名称：

  Approaches to the synthesis of CF2-analogues of 2-deoxy-2-aminoglycosides

  摘要：

  The preparation of a fluorinated C-glycosidic analogue of a 2-deoxy-2-acetamido-D-altrose is described. The synthetic sequence involves the addition of a difluoroenoxysilane to a D-glucal, an epoxidation of the resulting unsaturated CF2-glycoside and a ring-opening reaction with TMSN3. An Overman rearrangement of the unsaturated intermediate is also described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.155

文献信息

• Approaches to the synthesis of CF2-analogues of 2-deoxy-2-aminoglycosides
  作者：Florent Poulain、Eric Leclerc、Jean-Charles Quirion

  DOI：10.1016/j.tetlet.2009.01.155

  日期：2009.4

  The preparation of a fluorinated C-glycosidic analogue of a 2-deoxy-2-acetamido-D-altrose is described. The synthetic sequence involves the addition of a difluoroenoxysilane to a D-glucal, an epoxidation of the resulting unsaturated CF2-glycoside and a ring-opening reaction with TMSN3. An Overman rearrangement of the unsaturated intermediate is also described. (C) 2009 Elsevier Ltd. All rights reserved.