methyl 2-benzamido-3,6-di-O-benzoyl-2-deoxy-α-D-galactopyranoside | 32449-74-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-benzamido-3,6-di-O-benzoyl-2-deoxy-α-D-galactopyranoside
• 英文别名: [(2R,3R,4R,5R,6S)-5-benzamido-4-benzoyloxy-3-hydroxy-6-methoxyoxan-2-yl]methyl benzoate
• CAS: 32449-74-4
• 化学式: C₂₈H₂₇NO₈
• 分子量: 505.524
• InChiKey: NHPFHXWMDGBVNF-NRUNVSGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2-benzamido-3,6-di-O-benzoyl-2-deoxy-α-D-galactopyranoside 在 吡啶 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 1.5h， 生成 methyl 4-S-acetyl-2-benzamido-3,6-di-O-benzoyl-2-deoxy-4-thio-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 4-C-sulfoaminosugar derivatives: isomerization of 4-C-sulfogalactosamine to its gluco epimer

  摘要：

  Methyl 2-benzamido-3,6-di-O-benzoyl-2,4-dideoxy-alpha-D-glucopyranoside-4-C-sulfonate sodium salt 9 and its galacto epimer 10 were prepared by oxidation with hydrogen peroxide in acetic acid of methyl 4-S-acetyl-2-benzamido-3,6-di-O-benzoyl-2-deoxy-4-thio-alpha-D-glucopyranoside 7 and its galacto epimer 8, respectively. The 4-thioglucoside 7 was prepared from methyl 2-benzamido-3,6-di-O-benzoyl-2-deoxy-alpha-D-glucopyranoside by double inversion through triflation, inversion at C-4 with NaNO2, triflation of the resulting methyl 2-benzamido-3,6-di-O-benzoyl-2-deoxy-alpha-D-galactopyranoside, followed by displacement with potassium thioacetate. Deacylation of 9 with refluxing aqueous sodium hydroxide followed by deionisation yielded methyl 2-amino-2,4-dideoxy-alpha-D-glucopyranoside-4-C-sulfonic acid 11. Deacylation of the galactopyranoside 10 under the same conditions also gave 11, due to base catalysed isomerisation of galacto to the more stable gluco configuration. The structure of 11, crystallized as the monohydrate, was confirmed by X-ray crystallographic analysis. The asymmetric unit contains two sugar molecules in two unique but similar conformations and two water molecules. The sulfo and the amino groups form a zwitterion, with each ammonium group hydrogen bonded to the sulfonate groups of two other molecules related by symmetry. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.004
• 作为产物：
  描述：

  methyl 2-benzamido-3,6-di-O-benzoyl-2-deoxy-4-O-trifluoromethanesulfonyl-α-D-glucopyranoside 在 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以2.4 g的产率得到methyl 2-benzamido-3,6-di-O-benzoyl-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of 4-C-sulfoaminosugar derivatives: isomerization of 4-C-sulfogalactosamine to its gluco epimer

  摘要：

  Methyl 2-benzamido-3,6-di-O-benzoyl-2,4-dideoxy-alpha-D-glucopyranoside-4-C-sulfonate sodium salt 9 and its galacto epimer 10 were prepared by oxidation with hydrogen peroxide in acetic acid of methyl 4-S-acetyl-2-benzamido-3,6-di-O-benzoyl-2-deoxy-4-thio-alpha-D-glucopyranoside 7 and its galacto epimer 8, respectively. The 4-thioglucoside 7 was prepared from methyl 2-benzamido-3,6-di-O-benzoyl-2-deoxy-alpha-D-glucopyranoside by double inversion through triflation, inversion at C-4 with NaNO2, triflation of the resulting methyl 2-benzamido-3,6-di-O-benzoyl-2-deoxy-alpha-D-galactopyranoside, followed by displacement with potassium thioacetate. Deacylation of 9 with refluxing aqueous sodium hydroxide followed by deionisation yielded methyl 2-amino-2,4-dideoxy-alpha-D-glucopyranoside-4-C-sulfonic acid 11. Deacylation of the galactopyranoside 10 under the same conditions also gave 11, due to base catalysed isomerisation of galacto to the more stable gluco configuration. The structure of 11, crystallized as the monohydrate, was confirmed by X-ray crystallographic analysis. The asymmetric unit contains two sugar molecules in two unique but similar conformations and two water molecules. The sulfo and the amino groups form a zwitterion, with each ammonium group hydrogen bonded to the sulfonate groups of two other molecules related by symmetry. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.004

文献信息

• Synthesis of 4-C-sulfoaminosugar derivatives: isomerization of 4-C-sulfogalactosamine to its gluco epimer
  作者：José G. Fernández-Bolaños、Salud Garcı́a、José Fernández-Bolaños、Ma Jesús Diánez、Ma Dolores Estrada、Amparo López-Castro、Simeón Pérez-Garrido

  DOI：10.1016/j.tetasy.2003.10.004

  日期：2003.11

  Methyl 2-benzamido-3,6-di-O-benzoyl-2,4-dideoxy-alpha-D-glucopyranoside-4-C-sulfonate sodium salt 9 and its galacto epimer 10 were prepared by oxidation with hydrogen peroxide in acetic acid of methyl 4-S-acetyl-2-benzamido-3,6-di-O-benzoyl-2-deoxy-4-thio-alpha-D-glucopyranoside 7 and its galacto epimer 8, respectively. The 4-thioglucoside 7 was prepared from methyl 2-benzamido-3,6-di-O-benzoyl-2-deoxy-alpha-D-glucopyranoside by double inversion through triflation, inversion at C-4 with NaNO2, triflation of the resulting methyl 2-benzamido-3,6-di-O-benzoyl-2-deoxy-alpha-D-galactopyranoside, followed by displacement with potassium thioacetate. Deacylation of 9 with refluxing aqueous sodium hydroxide followed by deionisation yielded methyl 2-amino-2,4-dideoxy-alpha-D-glucopyranoside-4-C-sulfonic acid 11. Deacylation of the galactopyranoside 10 under the same conditions also gave 11, due to base catalysed isomerisation of galacto to the more stable gluco configuration. The structure of 11, crystallized as the monohydrate, was confirmed by X-ray crystallographic analysis. The asymmetric unit contains two sugar molecules in two unique but similar conformations and two water molecules. The sulfo and the amino groups form a zwitterion, with each ammonium group hydrogen bonded to the sulfonate groups of two other molecules related by symmetry. (C) 2003 Elsevier Ltd. All rights reserved.