[(2R)-2-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-prop-2-enoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-prop-2-enoxyethyl] trifluoromethanesulfonate | 151075-98-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: [(2R)-2-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-prop-2-enoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-prop-2-enoxyethyl] trifluoromethanesulfonate
• CAS: 151075-98-8
• 化学式: C₁₆H₂₃F₃O₈S
• 分子量: 432.415
• InChiKey: LVWOHEXIXXUYFB-RKQHYHRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  [(2R)-2-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-prop-2-enoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-prop-2-enoxyethyl] trifluoromethanesulfonate 在 sodium dihydrogenphosphate 、 sodium amalgam 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 甲苯 为溶剂， 反应 0.25h， 生成 3,5-O-allyl-6-deoxy-6-diethyl(1'-fluoro)phosphonomethyl-1,2-O-isopropylidene-α-D-glucofuranoside
  参考文献：
  名称：

  A Convergent Triflate Displacement Approach to (α-Monofluoroalkyl)phosphonates

  摘要：

  Treatment of primary alkyl triflates or iodides with the potassium salt of diethyl (alpha -fluoro-alpha -phenylsulfonyl methyl)phosphonate yields (alpha -fluoro-alpha -phenylsulfonylalkyl)phosphonate These can be cleanly desulfonated, in a matter of minutes, with Na(HS) in MeOH/THF/NaH2PO4. This two-step procedure complements previously reported triflate displacement approaches to alpha -nonfluorinated and alpha,alpha -difluorinated phosphonates.

  DOI：

  10.1021/ol015983z
• 作为产物：
  描述：

  三氟甲磺酸酐 、 (R)-2-Allyloxy-2-((3aR,5R,6S,6aR)-6-allyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethanol 在 2,6-二叔丁基-4-甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到[(2R)-2-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-prop-2-enoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-prop-2-enoxyethyl] trifluoromethanesulfonate
  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.