N-(3,4,6-tri-O-benzyl-2-O-mesyl-β-D-galactopyranosyl)triphenylphosphine imide | 1333933-40-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3,4,6-tri-O-benzyl-2-O-mesyl-β-D-galactopyranosyl)triphenylphosphine imide
• 英文别名: [(2R,3R,4S,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-[(triphenyl-lambda5-phosphanylidene)amino]oxan-3-yl] methanesulfonate；[(2R,3R,4S,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-[(triphenyl-λ5-phosphanylidene)amino]oxan-3-yl] methanesulfonate
• CAS: 1333933-40-6
• 化学式: C₄₆H₄₆NO₇PS
• 分子量: 787.913
• InChiKey: PPTKZXXWZUZHJW-JQIFVRNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  56
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-(3,4,6-tri-O-benzyl-2-O-mesyl-β-D-galactopyranosyl)triphenylphosphine imide 在 碳酸氢钠 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 8.0h， 生成 pent-4-enyl 2-allyloxycarbonylamino-3,4,6-tri-O-benzyl-2-deoxy-α-D-talopyranoside
  参考文献：
  名称：

  Epoxidation of glycals with oxone–acetone–tetrabutylammonium hydrogen sulfate: a convenient access to simple β-d-glycosides and to α-d-mannosamine and d-talosamine donors

  摘要：

  The addition of a phase transfer catalyst during the epoxidation of perbenzylated glycals with oxone-acetone under biphasic conditions allows their complete epoxidation. The epoxides were readily transformed into methyl 1,2-trans-beta-D-glycosides or 1,2-trans-beta-D-glycopyranosyl azides (D-gluco and-D-galacto configurations) bearing a free hydroxyl group at the 2-position. These glycosyl azides were converted to alkyl 1,2-trans-2-acetamido-2-deoxy-alpha-D-pyranosides or alkyl 2-allyloxycarbonylamino-2deoxy-alpha-D-pyranosides (D-manno and D-talo configurations) by a Staudinger reaction and a double inversion of configuration at C-1 and C-2. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.027
• 作为产物：
  描述：

  1,2-anhydro-3,4,6-tri-O-benzyl-D-galactopyranose 在 吡啶 、 sodium azide 、 四丁基硫酸氢铵 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 20.0h， 生成 N-(3,4,6-tri-O-benzyl-2-O-mesyl-β-D-galactopyranosyl)triphenylphosphine imide
  参考文献：
  名称：

  Epoxidation of glycals with oxone–acetone–tetrabutylammonium hydrogen sulfate: a convenient access to simple β-d-glycosides and to α-d-mannosamine and d-talosamine donors

  摘要：

  The addition of a phase transfer catalyst during the epoxidation of perbenzylated glycals with oxone-acetone under biphasic conditions allows their complete epoxidation. The epoxides were readily transformed into methyl 1,2-trans-beta-D-glycosides or 1,2-trans-beta-D-glycopyranosyl azides (D-gluco and-D-galacto configurations) bearing a free hydroxyl group at the 2-position. These glycosyl azides were converted to alkyl 1,2-trans-2-acetamido-2-deoxy-alpha-D-pyranosides or alkyl 2-allyloxycarbonylamino-2deoxy-alpha-D-pyranosides (D-manno and D-talo configurations) by a Staudinger reaction and a double inversion of configuration at C-1 and C-2. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.027

文献信息

• Epoxidation of glycals with oxone–acetone–tetrabutylammonium hydrogen sulfate: a convenient access to simple β-d-glycosides and to α-d-mannosamine and d-talosamine donors
  作者：Dominique Lafont、Joseph D’Attoma、Rejane Gomez、Peter G. Goekjian

  DOI：10.1016/j.tetasy.2011.06.027

  日期：2011.6

  The addition of a phase transfer catalyst during the epoxidation of perbenzylated glycals with oxone-acetone under biphasic conditions allows their complete epoxidation. The epoxides were readily transformed into methyl 1,2-trans-beta-D-glycosides or 1,2-trans-beta-D-glycopyranosyl azides (D-gluco and-D-galacto configurations) bearing a free hydroxyl group at the 2-position. These glycosyl azides were converted to alkyl 1,2-trans-2-acetamido-2-deoxy-alpha-D-pyranosides or alkyl 2-allyloxycarbonylamino-2deoxy-alpha-D-pyranosides (D-manno and D-talo configurations) by a Staudinger reaction and a double inversion of configuration at C-1 and C-2. (C) 2011 Elsevier Ltd. All rights reserved.