3,4,6-tri-O-benzyl-2-O-mesyl-β-D-galactopyranosyl azide | 1333933-31-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-benzyl-2-O-mesyl-β-D-galactopyranosyl azide
• 英文别名: [(2R,3R,4S,5S,6R)-2-azido-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] methanesulfonate
• CAS: 1333933-31-5
• 化学式: C₂₈H₃₁N₃O₇S
• 分子量: 553.636
• InChiKey: GNJDKJGUAHATJL-QBROEMLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-benzyl-2-O-mesyl-β-D-galactopyranosyl azide 在 碳酸氢钠 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 24.0h， 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：

  3,4,6-三邻苄基半乳醛 在 吡啶 、 Oxone 、 sodium azide 、 四丁基硫酸氢铵 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 6.5h， 生成 3,4,6-tri-O-benzyl-2-O-mesyl-β-D-galactopyranosyl azide
  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.