allyl 2-acetamido-6-O-benzyl-2-deoxy-3,4-O-dibenzoyl-α-D-glucopyranoside | 191925-22-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-acetamido-6-O-benzyl-2-deoxy-3,4-O-dibenzoyl-α-D-glucopyranoside
• CAS: 191925-22-1
• 化学式: C₃₂H₃₃NO₈
• 分子量: 559.616
• InChiKey: CMRXOVSENZEAKJ-BFGNKNHRSA-N

物化性质

• 沸点：
  724.0±60.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  109.39
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  allyl 2-acetamido-6-O-benzyl-2-deoxy-3,4-O-dibenzoyl-α-D-glucopyranoside 在 sodium hydroxide 、 水 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以62.3%的产率得到allyl 2-acetamido-6-O-benzyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Potential HIV protease inhibitors: Preparation of di-N-alkylated 2-, 6-, and 2,6-aminodeoxy-derivatives of d-glucose by direct displacement and by a novel reductive-alkylation procedure

  摘要：

  Glucose derivatives carrying branched lipophilic groups at the 2-, 6-, and 2,6-positions were required for biological testing as inhibitors of the protease produced by the human immunodeficiency virus. The synthesis of (N-benzyl-N-ethyl)-2-, 6- and 2,6-diaminodeoxy-D-glucose derivatives is described. The 2-tert-amino group was introduced by a two-step reductive alkylation procedure. The novel tertiary aminosugar, 2,6-di-(N-benzyl-N-ethyl)amino-2,6-dideoxy-D-glucose, was made via direct substitution of the sulphonate group in allyl 2-acetamido-2-deoxy-6-O-tosyl-D-glucopyranoside with N-benzylethylamine. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00039-6
• 作为产物：
  描述：

  allyl 2-acetamido-3-O-benzoyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 在 吡啶 、 3 A molecular sieve 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 allyl 2-acetamido-6-O-benzyl-2-deoxy-3,4-O-dibenzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Potential HIV protease inhibitors: Preparation of di-N-alkylated 2-, 6-, and 2,6-aminodeoxy-derivatives of d-glucose by direct displacement and by a novel reductive-alkylation procedure

  摘要：

  Glucose derivatives carrying branched lipophilic groups at the 2-, 6-, and 2,6-positions were required for biological testing as inhibitors of the protease produced by the human immunodeficiency virus. The synthesis of (N-benzyl-N-ethyl)-2-, 6- and 2,6-diaminodeoxy-D-glucose derivatives is described. The 2-tert-amino group was introduced by a two-step reductive alkylation procedure. The novel tertiary aminosugar, 2,6-di-(N-benzyl-N-ethyl)amino-2,6-dideoxy-D-glucose, was made via direct substitution of the sulphonate group in allyl 2-acetamido-2-deoxy-6-O-tosyl-D-glucopyranoside with N-benzylethylamine. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00039-6