allyl 2,6-di-(N-benzyl-N-ethyl)amino-2,6-dideoxy-α-D-glucopyranoside | 191925-53-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,6-di-(N-benzyl-N-ethyl)amino-2,6-dideoxy-α-D-glucopyranoside
• 英文别名: (2R,3S,4R,5R,6S)-5-[benzyl(ethyl)amino]-2-[[benzyl(ethyl)amino]methyl]-6-prop-2-enoxyoxane-3,4-diol
• CAS: 191925-53-8
• 化学式: C₂₇H₃₈N₂O₄
• 分子量: 454.61
• InChiKey: LVLFWDZQPYMUSY-ACFIUOAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  65.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  allyl 2,6-di-(N-benzyl-N-ethyl)amino-2,6-dideoxy-α-D-glucopyranoside 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以80%的产率得到propenyl 2,6-di-(N-benzyl-N-ethyl)amino-2,6-dideoxy-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-amino-6-(N-benzyl-N-ethyl)amino-2,6-dideoxy-α-D-glucopyranoside 在 sodium tetrahydroborate 作用下， 以 甲醇 、 苯 为溶剂， 反应 4.5h， 生成 allyl 2,6-di-(N-benzyl-N-ethyl)amino-2,6-dideoxy-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

文献信息

• 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
  作者：Jiaqiang Cai、Bruce E. Davison、C.Robin Ganellin、Suvit Thaisrivongs、Keith S. Wibley

  DOI：10.1016/s0008-6215(97)00039-6

  日期：1997.5

  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.