Trifluoro-methanesulfonic acid (2R,3R,4S,5R,6R)-3,4,5-tris-allyloxy-6-benzyloxy-tetrahydro-pyran-2-ylmethyl ester | 151075-90-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Trifluoro-methanesulfonic acid (2R,3R,4S,5R,6R)-3,4,5-tris-allyloxy-6-benzyloxy-tetrahydro-pyran-2-ylmethyl ester
• 英文别名: allyl(-2)[allyl(-3)][allyl(-4)][Tf(-6)]Glc(b)-O-Bn；[(2R,3R,4S,5R,6R)-6-phenylmethoxy-3,4,5-tris(prop-2-enoxy)oxan-2-yl]methyl trifluoromethanesulfonate
• CAS: 151075-90-0
• 化学式: C₂₃H₂₉F₃O₈S
• 分子量: 522.54
• InChiKey: VSUPOZLIBDNLCT-QMCAAQAGSA-N

物化性质

• 沸点：
  545.1±50.0 °C(predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  35
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  二氟甲基膦酸二乙酯 、 Trifluoro-methanesulfonic acid (2R,3R,4S,5R,6R)-3,4,5-tris-allyloxy-6-benzyloxy-tetrahydro-pyran-2-ylmethyl ester 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到[1,1-Difluoro-2-((2R,3R,4S,5R,6R)-3,4,5-tris-allyloxy-6-benzyloxy-tetrahydro-pyran-2-yl)-ethyl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  Synthesis of (.alpha.,.alpha.-difluoroalkyl)phosphonates by displacement of primary triflates

  摘要：

  Simple primary alkyl triflates and those derived from several monosaccharides are cleanly displaced by diethyl (lithiodifluoromethyl)phosphonate to provide the corresponding (alpha,alpha-difluoroalkyl)phosphonates in minutes at -78-degrees-C.

  DOI：

  10.1021/jo00075a005
• 作为产物：
  描述：

  三氟甲磺酸酐 、 ((2R,3R,4S,5R,6R)-3,4,5-Tris-allyloxy-6-benzyloxy-tetrahydro-pyran-2-yl)-methanol 在 2,6-二叔丁基-4-甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到Trifluoro-methanesulfonic acid (2R,3R,4S,5R,6R)-3,4,5-tris-allyloxy-6-benzyloxy-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Synthesis of (.alpha.,.alpha.-difluoroalkyl)phosphonates by displacement of primary triflates

  摘要：

  Simple primary alkyl triflates and those derived from several monosaccharides are cleanly displaced by diethyl (lithiodifluoromethyl)phosphonate to provide the corresponding (alpha,alpha-difluoroalkyl)phosphonates in minutes at -78-degrees-C.

  DOI：

  10.1021/jo00075a005

文献信息

• Facile installation of the phosphonate and (α,α-difluoromethyl)phosphonate functionalities equipped with benzyl protection
  作者：David B. Berkowitz、Debnath Bhuniya、Gorka Peris

  DOI：10.1016/s0040-4039(99)00077-5

  日期：1999.3

  Under appropriate conditions, dibenzyl (lithiomethyl)phosphonate and dibenzyl (lithiodifluoromethyl)phosphonate displace primary triflates to provide convenient access to the corresponding phosphonates, carrying benzyl ester protecting groups. This approach is of particular advantage for phosphonate ester deprotection, which may be achieved by simple hydrogenolysis. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of (.alpha.,.alpha.-difluoroalkyl)phosphonates by displacement of primary triflates
  作者：David B. Berkowitz、MariJean Eggen、Quanrong Shen、Darby G. Sloss

  DOI：10.1021/jo00075a005

  日期：1993.11

  Simple primary alkyl triflates and those derived from several monosaccharides are cleanly displaced by diethyl (lithiodifluoromethyl)phosphonate to provide the corresponding (alpha,alpha-difluoroalkyl)phosphonates in minutes at -78-degrees-C.