allyl 6-O-benzyl-2-benzylamino-2-deoxy-α-D-glucopyranoside | 191925-30-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 6-O-benzyl-2-benzylamino-2-deoxy-α-D-glucopyranoside
• CAS: 191925-30-1
• 化学式: C₂₃H₂₉NO₅
• 分子量: 399.487
• InChiKey: GDIZKGSVCQOPSC-JLMDMGSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  29.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  80.18
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  allyl 6-O-benzyl-2-benzylamino-2-deoxy-α-D-glucopyranoside 在 盐酸 、 sodium tetrahydroborate 、 potassium tert-butylate 、 水 作用下， 以 二甲基亚砜 、 丙酮 为溶剂， 反应 11.0h， 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：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以4.0 g的产率得到allyl 6-O-benzyl-2-benzylamino-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