benzyl 6-deoxy-6-diethyl-(1'-fluoro-1'-phenylsulfonyl)phosphonomethyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside | 352438-95-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 6-deoxy-6-diethyl-(1'-fluoro-1'-phenylsulfonyl)phosphonomethyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-[2-(benzenesulfonyl)-2-diethoxyphosphoryl-2-fluoroethyl]-3,4,5,6-tetrakis(phenylmethoxy)oxane
• CAS: 352438-95-0
• 化学式: C₄₅H₅₀FO₁₀PS
• 分子量: 832.924
• InChiKey: FGWDVPLRNFJNSI-XCDRTOGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  58
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  benzyl 6-deoxy-6-diethyl-(1'-fluoro-1'-phenylsulfonyl)phosphonomethyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside 在 偶氮二异丁腈 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 6.0h， 以71%的产率得到benzyl 6-deoxy-6-(1'-fluoro)phenylsulfonylmethyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside
  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：

  氟代（苯磺酰）甲基膦酸二乙酯 、 benzyl 2,3,4-tri-O-benzyl-6-O-trifluoromethanesulfonyl-β-D-glucopyranoside 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 甲苯 为溶剂， 反应 0.08h， 以60%的产率得到benzyl 6-deoxy-6-diethyl-(1'-fluoro-1'-phenylsulfonyl)phosphonomethyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside
  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

文献信息

• A Convergent Triflate Displacement Approach to (α-Monofluoroalkyl)phosphonates
  作者：David B. Berkowitz、Mohua Bose、Nathan G. Asher

  DOI：10.1021/ol015983z

  日期：2001.6.1

  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.