allyl 2-amino-6-O-benzyl-2-deoxy-α-D-glucopyranoside | 191925-27-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-amino-6-O-benzyl-2-deoxy-α-D-glucopyranoside
• CAS: 191925-27-6
• 化学式: C₁₆H₂₃NO₅
• 分子量: 309.362
• InChiKey: WNWALMQHSHDFSH-QCODTGAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.18
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  94.17
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  allyl 2-amino-6-O-benzyl-2-deoxy-α-D-glucopyranoside 在 盐酸 、 sodium tetrahydroborate 、 potassium tert-butylate 、 水 作用下， 以 甲醇 、 二甲基亚砜 、 丙酮 、 苯 为溶剂， 反应 12.5h， 生成 N,6-O-dibenzyl-N-ethyl-D-glucosamine
  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-6-O-benzyl-2-deoxy-α-D-glucopyranoside 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 15.0h， 以95.2%的产率得到allyl 2-amino-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