2,2,2-Trifluoro-N-phenyl-acetimidic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl ester | 607714-24-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,2-Trifluoro-N-phenyl-acetimidic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl ester
• CAS: 607714-24-9
• 化学式: C₄₁H₄₈F₃NO₆Si
• 分子量: 735.916
• InChiKey: ZJMIGANJXPAMAL-OXODQGHPSA-N

物化性质

• 沸点：
  681.3±65.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  52.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  67.74
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  双丙酮半乳糖 、 2,2,2-Trifluoro-N-phenyl-acetimidic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl ester 在 ytterbium(III) triflate 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 反应 12.0h， 以72%的产率得到
  参考文献：
  名称：

  An approach to the highly stereocontrolled synthesis of α-glycosides. Compatible use of the very acid labile dimethoxytrityl protecting group with Yb(OTf)3-promoted glycosidation

  摘要：

  The very acid labile dimethoxytrityl group is demonstrated to survive Yb(OTf)(3)-promoted glycosidations with N-phenyl trifluoroacetimidates as the donors. In addition, the installation of this sterically demanding protecting group at the primary position of the donor allows the achievement of a very high selectivity in the synthesis of alpha-glycosides with a variety of saccharidic acceptors. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01541-7
• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-D-glucopyranose 在 咪唑 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2,2,2-Trifluoro-N-phenyl-acetimidic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl ester
  参考文献：
  名称：

  An approach to the highly stereocontrolled synthesis of α-glycosides. Compatible use of the very acid labile dimethoxytrityl protecting group with Yb(OTf)3-promoted glycosidation

  摘要：

  The very acid labile dimethoxytrityl group is demonstrated to survive Yb(OTf)(3)-promoted glycosidations with N-phenyl trifluoroacetimidates as the donors. In addition, the installation of this sterically demanding protecting group at the primary position of the donor allows the achievement of a very high selectivity in the synthesis of alpha-glycosides with a variety of saccharidic acceptors. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01541-7